Intermediates to prepare herbicidal pyrimidone derivatives

ABSTRACT

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, 
     
       
         
         
             
             
         
       
         
         
           
             X is CH or N; 
             Y is C(O) or S(O) 2 ; provided that when Y is S(O) 2 , then X is CH; 
             A is a radical selected from the group consisting of 
           
         
       
    
                         
and B 1 , B 2 , B 3 , T, R 1 , R 2  R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12  and R 13  are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

FIELD OF THE INVENTION

This invention relates to certain bis-nitrogen heterocycles, their saltsand compositions, and methods of their use for controlling undesirablevegetation. This invention also relates to certain intermediates and amethod useful for preparing these bis-nitrogen heterocycles and theirsalts. This invention als relates to certain bis-nitrogen oxo or sulfonoheterocycles, their salts and compositions, and methods of their use forcontrolling undesirable vegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achievinghigh crop efficiency. Achievement of selective control of the growth ofweeds especially in such useful crops as rice, soybean, sugar beet,maize, potato, wheat, barley, tomato and plantation crops, among others,is very desirable. Unchecked weed growth in such useful crops can causesignificant reduction in productivity and thereby result in increasedcosts to the consumer. The control of undesired vegetation in noncropareas is also important. Many products are commercially available forthese purposes, but the need continues for new compounds that are moreeffective, less costly, less toxic, environmentally safer or havedifferent sites of action.

International patent application publication WO 2007/088876 disclosespyridone compounds of Formula i

wherein inter alia R₁ is C₁-C₆ alkyl; R₂ and R₃ are each independentlyhydrogen, cyano, or nitro; and A is a A-1 through A-5 as defined thereinas herbicides.

The bis-nitrogen containing oxo and sulfono heterocycles of the presentinvention are not disclosed in this publication.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 (including allstereoisomers), N-oxides, and salts thereof, agricultural compositionscontaining them and their use as herbicides:

wherein

-   -   X is CH;    -   Y is C(O);    -   A is a radical selected from the group consisting of

-   -   B¹ and B³ are each independently a radical selected from the        group consisting of

-   -   B² is a radical selected from the group consisting of

-   -   R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),        —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each        optionally substituted on ring members with up to five        substituents selected from R²¹; or -G or —W²G; or cyano,        hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂,        —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₁₀ alkyl, C₂-C₁₀ alkenyl, C₂-C₁₀        alkynyl, C₁-C₁₀ haloalkyl, C₂-C₁₀ haloalkenyl, C₂-C₁₂        haloalkynyl, C₃-C₁₂ cycloalkyl, C₃-C₁₂ halocycloalkyl, C₄-C₁₄        alkylcycloalkyl, C₄-C₁₄ cycloalkylalkyl, C₆-C₁₈        cycloalkylcycloalkyl, C₄-C₁₄ halocycloalkylalkyl, C₅-C₁₆        alkylcycloalkylalkyl, C₃-C₁₂ cycloalkenyl, C₃-C₁₂        halocycloalkenyl, C₂-C₁₂ alkoxyalkyl, C₃-C₁₂ alkoxyalkenyl,        C₄-C₁₄ alkylcycloalkyl, C₄-C₁₄ alkoxycycloalkyl, C₄-C₁₄        cycloalkoxyalkyl, C₅-C₁₄ cycloalkoxyalkoxyalkyl, C₃-C₁₄        alkoxyalkoxyalkyl, C₂-C₁₂ alkylthioalkyl, C₂-C₁₂        alkylsulfinylalkyl, C₂-C₁₂ alkylsulfonylalkyl, C₂-C₁₂        alkylaminoalkyl, C₃-C₁₄ dialkylaminoalkyl, C₂-C₁₂        haloalkylaminoalkyl, C₄-C₁₄ cycloalkylaminoalkyl, C₂-C₁₂        alkylcarbonyl, C₂-C₁₂ haloalkylcarbonyl, C₄-C₁₄        cycloalkylcarbonyl, C₂-C₁₂ alkoxycarbonyl, C₄-C₁₆        cycloalkoxycarbonyl, C₅-C₁₄ cycloalkylalkoxycarbonyl, C₂-C₁₂        alkylaminocarbonyl, C₃-C₁₄ dialkylaminocarbonyl, C₄-C₁₄        cycloalkylaminocarbonyl, C₂-C₉ cyanoalkyl, C₁-C₁₀ hydroxyalkyl,        C₄-C₁₄ cycloalkenylalkyl, C₂-C₁₂ haloalkoxyalkyl, C₂-C₁₂        alkoxyhaloalkyl, C₂-C₁₂ haloalkoxyhaloalkyl, C₄-C₁₄        halocycloalkoxyalkyl, C₄-C₁₄ cycloalkenyloxyalkyl, C₄-C₁₄        halocycloalkenyloxyalkyl, C₃-C₁₄ dialkoxyalkyl, C₃-C₁₄        alkoxyalkylcarbonyl, C₃-C₁₄ alkoxycarbonylalkyl, C₂-C₁₂        haloalkoxycarbonyl, C₁-C₁₀ alkoxy, C₁-C₁₀ haloalkoxy, C₃-C₁₂        cycloalkoxy, C₃-C₁₂ halocycloalkoxy, C₄-C₁₄ cycloalkylalkoxy,        C₂-C₁₀ alkenyloxy, C₂-C₁₀ haloalkenyloxy, C₂-C₁₀ alkynyloxy,        C₃-C₁₀ haloalkynyloxy, C₂-C₁₂ alkoxyalkoxy, C₂-C₁₂        alkylcarbonyloxy, C₂-C₁₂ haloalkylcarbonyloxy, C₄-C₁₄        cycloalkylcarbonyloxy, C₃-C₁₄ alkylcarbonylalkoxy, C₁-C₁₀        alkylthio, C₁-C₁₀ haloalkylthio, C₃-C₁₂ cycloalkylthio, C₁-C₁₀        alkylsulfinyl, C₁-C₁₀ haloalkylsulfinyl, C₁-C₁₀ alkylsulfonyl,        C₁-C₁₀ haloalkylsulfonyl, C₃-C₁₂ cycloalkylsulfonyl, C₂-C₁₂        alkylcarbonylthio, C₂-C₁₂ alkyl(thiocarbonyl)thio, C₃-C₁₂        cycloalkylsulfinyl, C₁-C₁₀ alkylaminosulfonyl, C₂-C₁₂        dialkylaminosulfonyl, C₁-C₁₀ alkylamino, C₂-C₁₂ dialkylamino,        C₁-C₁₀ haloalkylamino, C₂-C₁₂ halodialkylamino, C₃-C₁₂        cycloalkylamino, C₂-C₁₂ alkylcarbonylamino, C₂-C₁₂        haloalkylcarbonylamino, C₁-C₁₀ alkylsulfonylamino, C₁-C₁₀        haloalkylsulfonylamino or C₄-C₁₄ cycloalkyl(alkyl)amino;    -   W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;    -   W² is C₁-C₆ alkylene;    -   R² is phenyl or —W³(phenyl), each optionally substituted on ring        members with up to five substituents selected from R²¹; or -G or        —W⁴G; or H, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH,        —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO₂NH₂,        —SO₂NHCN, —SO₂NHOH, —SF₅, —NHCHO, —NHNH₂, —NHOH, —NHCN,        —NHC(═O)NH₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆        haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈        cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀        halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀        alkoxyalkenyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀        alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈        alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈        alkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, C₂-C₈        haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈        alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀        cycloalkylaminocarbonyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl,        C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈        alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀        halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀        halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₃-C₁₀        alkoxyalkylcarbonyl, C₃-C₁₀ alkoxycarbonylalkyl, C₂-C₈        haloalkoxycarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy,        C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆        haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy,        C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀        alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈        cycloalkylsulfonyl, C₃-C₈ trialkylsilyl, C₃-C₈ cycloalkenyloxy,        C₃-C₈ halocycloalkenyloxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈        alkoxyhaloalkoxy, C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₁₀        alkoxycarbonylalkoxy, C₂-C₈ alkyl(thiocarbonyl)oxy, C₂-C₈        alkylcarbonylthio, C₂-C₈ alkyl(thiocarbonyl)thio, C₃-C₈        cycloalkylsulfinyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈        dialkylaminosulfonyl, C₃-C₁₀ halotrialkylsilyl, C₁-C₆        alkylamino, C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈        halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆        alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino or C₄-C₁₀        cycloalkyl(alkyl)amino; or    -   R¹ and R² are taken together along with the atoms to which they        are attached to make a 5-, 6- or 7-membered unsaturated,        partially unsaturated or fully unsaturated ring along with        members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or        2 sulfur atoms or up to two —S(O)—, —S(O)₂—, —C(O)— groups        optionally substituted on carbon atom ring members selected from        halogen, cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆        haloalkyl, C₃-C₈ cycloalkyl and C₂-C₈ alkoxyalkyl; and phenyl        optionally substituted with up to 5 substituents selected from        cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆        haloalkoxy; and optionally substituted on nitrogen ring members        selected from H and C₁-C₆ alkyl; and phenyl optionally        substituted with up to 5 substituents selected from cyano,        nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy;    -   W³ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;    -   W⁴ is C₁-C₆ alkylene;    -   R³ is H, halogen, cyano, hydroxy, —O⁻M⁺, amino, nitro, —CHO,        —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —SH, —SO₂NH₂, —SO₂NHCN,        —SO₂NHOH, —OCN, —SCN, —SF₅, —NHNH₂, —NHOH, —N═C═O, —N═C═S, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈        halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy,        C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy,        C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈        haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀        alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈        cycloalkylsulfonyl, C₁-C₆ alkylsulfonyloxy, C₁-C₆ alkylamino,        C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈        halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆        alkylsulfonylamino or C₁-C₆ haloalkylsulfonylamino; or        benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy,        phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio,        phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or        benzylsulfonyl, each optionally substituted on ring members with        up to five substituents selected from R²¹;    -   M⁺ is an alkali metal cation or an ammonium cation;    -   R⁴, R⁵, R⁶ and R⁷ are each independently H, halogen, hydroxy,        C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy or C₃-C₈        halocycloalkoxy; or phenyl or benzyl, each optionally        substituted on ring members with up to five substituents        selected from R²¹;    -   R⁸ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆        haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈        cycloalkyl or C₃-C₈ halocycloalkyl; or benzyl optionally        substituted on ring members with up to five substituents        selected from R²¹;    -   R⁹ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆        haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈        cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀        halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀        cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈        alkylthioalkyl;    -   R¹⁰ is H, halogen, cyano, hydroxy, amino, nitro, SH, —SO₂NH₂,        —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, —NHCHO, —NHNH₂, —N₃,        —NHOH, —NHCN, —NHC(═O)NH₂, —N═C═O, —N═C═S, C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈        halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl,        C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈ alkylthioalkyl;    -   R¹¹ is H, halogen, cyano, hydroxy, amino, C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀        halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀        cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl or C₂-C₈        alkylsulfonylalkyl; or phenyl optionally substituted with up to        five substituents selected from R²¹;    -   R¹² is H, halogen, cyano, hydroxy, amino, C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl        or C₂-C₈ alkoxycarbonylamino;    -   R¹³ is H, halogen, cyano, hydroxy, amino, nitro or C₂-C₈        alkoxycarbonyl;    -   n is 0, 1, or 2;    -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is independently H, halogen, cyano,        hydroxy or C₁-C₆ alkyl; or    -   a pair of R¹⁴ and R¹⁸ is taken together as C₂-C₆ alkylene or        C₂-C₆ alkenylene;    -   R²⁰ is H, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl or C₃-C₈ cycloalkyl;    -   T is C₁-C₆ alkylene or C₂-C₆ alkenylene;    -   each G is independently a 5- or 6-membered heterocyclic ring or        an 8-, 9- or 10-membered fused bicyclic ring system, each ring        or ring system optionally substituted with up to five        substituents selected from R²¹ on carbon ring members and R²² on        nitrogen ring members;    -   each R²¹ is independently halogen, cyano, hydroxy, amino, nitro,        —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH,        —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆        haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,        C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino,        C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈        cycloalkylamino; and    -   each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl.

More particularly, this invention pertains to a compound of Formula 1(including all stereoisomers), an N-oxide, or a salt thereof. Thisinvention also relates to a herbicidal composition comprising a compoundof the invention (i.e. in a herbicidally effective amount) and at leastone component selected from the group consisting of surfactants, soliddiluents and liquid diluents. This invention further relates to a methodfor controlling the growth of undesired vegetation comprising contactingthe vegetation or its environment with a herbicidally effective amountof a compound of the invention (e.g., as a composition described herein)

This invention also relates to a herbicidal mixture of (a) a compound ofFormula 1 and (b) at least one additional active ingredient.

This invention is also directed to an intermediate compound of Formula1Q (including all stereoisomers), N-oxides, and salts thereof:

wherein A′ is a radical selected from the group consisting of

R¹, R², B¹, B², B³, T, R⁹ and R¹⁰ are as defined above for a compound ofFormula 1 which is useful for preparing a compound of Formula 1.

This invention is also directed to a compound of Formula 1R (includingall stereoisomers), N-oxides, and salts thereof:

-   -   wherein    -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),        —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally        substituted on ring members with up to five substituents        selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈        cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈        alkylsulfinylalkyl or C₂-C₈ alkylsulfonylalkyl;    -   W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;    -   W² is C₁-C₆ alkylene;    -   R² is phenyl or —W³(phenyl), each substituted on ring members        with up to two substituents selected from R²¹; or -G; or C₁-C₆        alkyl or C₃-C₈ cycloalkyl;    -   W³ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;    -   each G is independently a 5- or 6-membered heterocyclic ring or        an 8-, 9- or 10-membered fused bicyclic ring system, each ring        or ring system optionally substituted with up to five        substituents selected from R²¹ on carbon ring members and R²² on        nitrogen ring members;    -   each R²¹ is independently halogen, cyano, hydroxy, amino, nitro,        —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH,        —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆        haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,        C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino,        C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈        cycloalkylamino; and    -   each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl        which is useful for preparing a compound of Formula 1.

This invention is also directed to a compound of Formula 1S (includingall stereoisomers), N-oxides, and salts thereof:

-   -   wherein    -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),        —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally        substituted on ring members with up to five substituents        selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈        cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl or C₂-C₈        alkylsulfonylalkyl;    -   W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;    -   W² is C₁-C₆ alkylene;    -   R² is phenyl or —W³(phenyl), each substituted on ring members        with up to two substituents selected from R²¹; or -G; or C₁-C₆        alkyl or C₃-C₈ cycloalkyl;    -   W³ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;    -   each G is independently a 5- or 6-membered heterocyclic ring or        an 8-, 9- or 10-membered fused bicyclic ring system, each ring        or ring system optionally substituted with up to five        substituents selected from R²¹ on carbon ring members and R²² on        nitrogen ring members;    -   each R²¹ is independently halogen, cyano, hydroxy, amino, nitro,        —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH,        —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆        haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,        C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino,        C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈        cycloalkylamino;    -   each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl;        and    -   R²³ is an optionally substituted carbon moiety        which is useful for preparing a compound of Formula 1.

This invention is also directed to a process for preparing a compound ofFormula 1 from a compound of formula 1Q in the presence of cesiumfluoride:

wherein A′ is a radical selected from A′-1, A′-2, A′-3 and A′-5 asdefined above for a compound of Formula 1Q; and A is radical selectedfrom A-1, A-2, A-3 and A-5 as defined above for a compound of Formula 1;and R¹ and R² are as defined above for a compound of Formula 1 which isuseful for preparing a compound of Formula 1.

This invention is also directed to compounds of Formula 1P (includingall stereoisomers), N-oxides, and salts thereof, agriculturalcompositions containing them and their use as herbicides:

wherein

-   -   X is CH or N;    -   Y is C(O) or S(O)₂; provided that when Y is S(O)₂, then X is CH;    -   A is a radical selected from the group consisting of

-   -   B¹ and B³ are each independently a radical selected from the        group consisting of

-   -   B² is a radical selected from the group consisting of

-   -   R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),        —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each        optionally substituted on ring members with up to five        substituents selected from R²¹; or -G or —W²G; or cyano,        hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂,        —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl,        C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl,        C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀        halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀        cycloalkoxyalkyl, C₅-C₁₀ cycloalkoxyalkoxyalkyl, C₃-C₁₀        alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈        alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈        alkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, C₂-C₈        haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈        alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀        cycloalkylaminocarbonyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl,        C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈        alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀        halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀        halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₃-C₁₀        alkoxyalkylcarbonyl, C₃-C₁₀ alkoxycarbonylalkyl, C₂-C₈        haloalkoxycarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy,        C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆        haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy,        C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀        alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈        cycloalkylsulfonyl, C₂-C₈ alkylcarbonylthio, C₂-C₈        alkyl(thiocarbonyl)thio, C₃-C₈ cycloalkylsulfinyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₁-C₆        alkylamino, C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈        halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆        alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino or C₄-C₁₀        cycloalkyl(alkyl)amino;    -   W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;    -   W² is C₁-C₆ alkylene;    -   R² is phenyl or —W³(phenyl), each optionally substituted on ring        members with up to five substituents selected from R²¹; or -G or        —W⁴G; or H, cyano, hydroxy, amino, nitro, —CHO, —C(═O)OH,        —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH, —SH, —SO₂NH₂,        —SO₂NHCN, —SO₂NHOH, —SF₅, —NHCHO, —NHNH₂, —NHOH, —NHCN,        —NHC(═O)NH₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆        haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈        cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀        halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀        cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₃-C₁₀        dialkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀        cycloalkylaminoalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂        cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₂-C₅        cyanoalkyl, C₁-C₆ hydroxyalkyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈        haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀        cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀        dialkoxyalkyl, C₃-C₁₀ alkoxyalkylcarbonyl, C₃-C₁₀        alkoxycarbonylalkyl, C₂-C₈ haloalkoxycarbonyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy,        C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy,        C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈ alkoxyalkoxy,        C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀        cycloalkylcarbonyloxy, C₃-C₁₀ alkylcarbonylalkoxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₃-C₈        trialkylsilyl, C₃-C₈ cycloalkenyloxy, C₃-C₈ halocycloalkenyloxy,        C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyhaloalkoxy, C₂-C₈        haloalkoxyhaloalkoxy, C₃-C₁₀ alkoxycarbonylalkoxy, C₂-C₈        alkyl(thiocarbonyl)oxy, C₂-C₈ alkylcarbonylthio, C₂-C₈        alkyl(thiocarbonyl)thio, C₃-C₈ cycloalkylsulfinyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        halotrialkylsilyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₁-C₆        haloalkylamino, C₂-C₈ halodialkylamino, C₃-C₈ cycloalkylamino,        C₂-C₈ alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆        alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino or C₄-C₁₀        cycloalkyl(alkyl)amino;    -   W³ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene;    -   W⁴ is C₁-C₆ alkylene;    -   R³ is H, halogen, cyano, hydroxy, —O⁻M⁺, amino, nitro, —CHO,        —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —SH, —SO₂NH₂, —SO₂NHCN,        —SO₂NHOH, —OCN, —SCN, —SF₅, —NHNH₂, —NHOH, —N═C═O, —N═C═S, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈        halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy,        C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy,        C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈        haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀        alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈        cycloalkylsulfonyl, C₁-C₆ alkylsulfonyloxy, C₁-C₆ alkylamino,        C₂-C₈ dialkylamino, C₁-C₆ haloalkylamino, C₂-C₈        halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆        alkylsulfonylamino or C₁-C₆ haloalkylsulfonylamino; or        benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy,        phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio,        phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or        benzylsulfonyl, each optionally substituted on ring members with        up to five substituents selected from R²¹;    -   M⁺ is an alkali metal cation or an ammonium cation;    -   R⁴, R⁵, R⁶ and R⁷ are each independently H, halogen, hydroxy,        C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,        C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy or C₃-C₈        halocycloalkoxy; or phenyl or benzyl, each optionally        substituted on ring members with up to five substituents        selected from R²¹;    -   R⁸ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆        haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈        cycloalkyl or C₃-C₈ halocycloalkyl; or benzyl optionally        substituted on ring members with up to five substituents        selected from R²¹;    -   R⁹ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆        haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈        cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀        halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀        cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈        alkylthioalkyl;    -   R¹⁰ is H, halogen, cyano, hydroxy, amino, nitro, SH, —SO₂NH₂,        —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, —NHCHO, —NHNH₂, —N₃,        —NHOH, —NHCN, —NHC(═O)NH₂, —N═C═O, —N═C═S, C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈        halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl,        C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈ alkylthioalkyl;    -   R¹¹ is H, halogen, cyano, hydroxy, amino, C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀        halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀        cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl or C₂-C₈        alkylsulfonylalkyl; or phenyl optionally substituted with up to        five substituents selected from R²¹;    -   R¹² is H, halogen, cyano, hydroxy, amino, C₁-C₆ alkyl, C₂-C₆        alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,        C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄        cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl        or C₂-C₈ alkoxycarbonylamino;    -   R¹³ is H, halogen, cyano, hydroxy, amino, nitro or C₂-C₈        alkoxycarbonyl;    -   n is 0, 1, or 2;    -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is independently H, halogen, cyano,        hydroxy or C₁-C₆ alkyl; or    -   a pair of R¹⁴ and R¹⁸ is taken together as C₂-C₆ alkylene or        C₂-C₆ alkenylene;    -   R²⁰ is H, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl or C₃-C₈ cycloalkyl; T is C₁-C₆ alkylene or C₂-C₆        alkenylene;    -   each G is independently a 5- or 6-membered heterocyclic ring or        an 8-, 9- or 10-membered fused bicyclic ring system, each ring        or ring system optionally substituted with up to five        substituents selected from R²¹ on carbon ring members and R²² on        nitrogen ring members;    -   each R²¹ is independently halogen, cyano, hydroxy, amino, nitro,        —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH,        —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆ alkyl,        C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆        haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,        C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino,        C₁-C₆ haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈        cycloalkylamino; and    -   each R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl.

More particularly, this invention pertains to a compound of Formula 1P(including all stereoisomers), an N-oxide, or a salt thereof. Thisinvention also relates to a herbicidal composition comprising a compoundof the invention (i.e. in a herbicidally effective amount) and at leastone component selected from the group consisting of surfactants, soliddiluents and liquid diluents. This invention further relates to a methodfor controlling the growth of undesired vegetation comprising contactingthe vegetation or its environment with a herbicidally effective amountof a compound of the invention (e.g., as a composition describedherein).

This invention also includes a herbicidal mixture of (a) a compound ofFormula 1P and (b) an active ingredient selected from a photosystem IIinhibitor.

DETAILS OF THE INVENTION

As used herein, the terms “comprises,” “comprising,” “includes,”“including,” “has,” “having,” “contains”, “containing,” “characterizedby” or any other variation thereof, are intended to cover anon-exclusive inclusion, subject to any limitation explicitly indicated.For example, a composition, mixture, process or method that comprises alist of elements is not necessarily limited to only those elements butmay include other elements not expressly listed or inherent to suchcomposition, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step, oringredient not specified. If in the claim, such would close the claim tothe inclusion of materials other than those recited except forimpurities ordinarily associated therewith. When the phrase “consistingof” appears in a clause of the body of a claim, rather than immediatelyfollowing the preamble, it limits only the element set forth in thatclause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define acomposition or method that includes materials, steps, features,components, or elements, in addition to those literally disclosed,provided that these additional materials, steps, features, components,or elements do not materially affect the basic and novelcharacteristic(s) of the claimed invention. The term “consistingessentially of” occupies a middle ground between “comprising” and“consisting of”.

Where applicants have defined an invention or a portion thereof with anopen-ended term such as “comprising,” it should be readily understoodthat (unless otherwise stated) the description should be interpreted toalso describe such an invention using the terms “consisting essentiallyof” or “consisting of.”

Further, unless expressly stated to the contrary, “or” refers to aninclusive “or” and not to an exclusive “or”. For example, a condition Aor B is satisfied by any one of the following: A is true (or present)and B is false (or not present), A is false (or not present) and B istrue (or present), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As referred to herein, the term “seedling”, used either alone or in acombination of words means a young plant developing from the embryo of aseed.

As referred to herein, the term “broadleaf” used either alone or inwords such as “broadleaf weed” means dicot or dicotyledon, a term usedto describe a group of angiosperms characterized by embryos having twocotyledons.

As used herein, the term “alkylating agent” refers to a chemicalcompound in which a carbon-containing radical is bound through a carbonatom to a leaving group such as halide or sulfonate, which isdisplaceable by bonding of a nucleophile to said carbon atom. Unlessotherwise indicated, the term “alkylating” does not limit thecarbon-containing radical to alkyl; the carbon-containing radicals inalkylating agents include the variety of carbon-bound substituentradicals specified for R¹, R² and R³.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkylene”denotes a straight-chain or branched alkanediyl. Examples of “alkylene”include CH₂, CH₂CH₂, CH(CH₃), CH₂CH₂CH₂, CH₂CH(CH₃) and the differentbutylene isomers. “Alkenylene” denotes a straight-chain or branchedalkenediyl containing one olefinic bond. Examples of “alkenylene”include CH═CH, CH₂CH═CH, CH═C(CH₃) and the different butenylene isomers.“Alkynylene” denotes a straight-chain or branched alkynediyl containingone triple bond. Examples of “alkynylene” include C≡C, CH₂C≡C, C≡CCH₂and the different butynylene isomers.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of“alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂and CH₃CH₂OCH₂CH₂. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy.“Alkenyloxy” includes straight-chain or branched alkenyloxy moieties.Examples of “alkenyloxy” include H₂C═CHCH₂O, (CH₃)₂C═CHCH₂O,(CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O. “Alkynyloxy”includes straight-chain or branched alkynyloxy moieties. Examples of“alkynyloxy” include HC≡CCH₂O, CH₃C≡CCH₂O and CH₃C≡CCH₂CH₂O.“Alkoxyalkenyl” includes straight-chain or branched alkenyl substitutedby an alkoxy group. Examples of “alkoxyalkenyl” include CH₃OCH═CH,CH₃C(OCH₃)═CH and CH₃CH₂OCH═CHCH₂. “Alkoxyalkoxyalkyl” denotesalkoxyalkoxy substitution on alkyl. Examples of “alkoxyalkoxyalkyl”include CH₃OCH₂OCH₂, CH₃OCH₂OCH₂CH₂, CH₃CH₂OCH₂OCH₂ andCH₃OCH₃CH₂OCH₂CH₂. “Alkylthio” includes branched or straight-chainalkylthio moieties such as methylthio, ethylthio, and the differentpropylthio, butylthio, pentylthio and hexylthio isomers. “Alkylsulfinyl”includes both enantiomers of an alkylsulfinyl group. Examples of“alkylsulfinyl” include CH₃S(O)—, CH₃CH₂S(O)—, CH₃CH₂CH₂S(O)—,(CH₃)₂CHS(O)— and the different butylsulfonyl, pentylsulfinyl andhexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH₃S(O)₂—,CH₃CH₂S(O)₂—, CH₃CH₂CH₂S(O)₂—, (CH₃)₂CHS(O)₂—, and the differentbutylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. The terms“cycloalkylsulfinyl” and “cycloalkylsulfonyl are defined analogously tothe terms “alkylsulfinyl” and “alkylsulfonyl” above.

“Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of“alkylthioalkyl” include CH₃SCH₂, CH₃SCH₂CH₂, CH₃CH₂SCH₂,CH₃CH₂CH₂CH₂SCH₂ and CH₃CH₂SCH₂CH₂; “alkylsulfinylalkyl” and“alkylsulfonylalkyl” include the corresponding sulfoxides and sulfones,respectively. “Alkylamino” includes an NH radical substituted withstraight-chain or branched alkyl. Examples of “alkylamino” includeCH₃CH₂NH, CH₃CH₂CH₂NH, and (CH₃)₂CHCH₂NH. Examples of “dialkylamino”include (CH₃)₂N, (CH₃CH₂CH₂)₂N and CH₃CH₂(CH₃)N. “Alkylaminoalkyl”denotes alkylamino substitution on alkyl. Examples of “alkylaminoalkyl”include CH₃NHCH₂, CH₃NHCH₂CH₂, CH₃CH₂NHCH₂, CH₃CH₂CH₂CH₂NHCH₂ andCH₃CH₂NHCH₂CH₂. Examples of “dialkylaminoalkyl” include ((CH₃)₂CH)₂NCH₂,(CH₃CH₂CH₂)₂NCH₂ and CH₃CH₂(CH₃)NCH₂CH₂. The term “alkylcarbonylamino”denotes alkyl bonded to a C(═O)NH moiety. Examples of“alkylcarbonylamino” include CH₃CH₂C(═O)NH and CH₃ CH₂CH₂C(═O)NH.

“Alkylcarbonylthio” denotes a straight-chain or branched alkylcarbonylattached to and linked through a sulfur atom. Examples of“alkylcarbonylthio” include CH₃C(═O)S, CH₃CH₂CH₂C(═O)S and(CH₃)₂CHC(═O)S. The term “alkyl(thiocarbonyl)oxy” refers to analkylsulfinyl moiety group bonded to an oxygen atom. Examples of“alkyl(thiocarbonyl)oxy”, include CH₃CH₂OS(O) and CH₃CH₂CH₂OS(O). Theterm “alkyl(thiocarbonyl)thio” refers to an alkylsulfinyl moiety bondedto a sulfur atom. Examples “alkyl(thiocarbonyl)thio” includeCH₃CH₂S(O)S.

“Trialkylsilyl” includes 3 branched and/or straight-chain alkyl radicalsattached to and linked through a silicon atom, such as trimethylsilyl,triethylsilyl and tert-butyldimethylsilyl. Examples of“halotrialkylsilyl” include CF₃(CH₃)₂Si—, (CF₃)₃Si—, and CH₂Cl(CH₃)₂Si—.“Hydroxyalkyl” denotes an alkyl group substituted with one hydroxygroup. Examples of “hydroxyalkyl” include HOCH₂CH₂, CH₃CH₂(OH)CH andHOCH₂CH₂CH₂CH₂. “Cyanoalkyl” denotes an alkyl group substituted with onecyano group. Examples of “cyanoalkyl” include NCCH₂, NCCH₂CH₂ andCH₃CH(CN)CH₂.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution ona cycloalkyl moiety and includes, for example, ethylcyclopropyl,i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term“cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety.Examples of “cycloalkylalkyl” include cyclopropylmethyl,cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chainor branched alkyl groups. The term “cycloalkoxy” denotes cycloalkyllinked through an oxygen atom such as cyclopentyloxy and cyclohexyloxy.The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkylmoiety. Examples of “alkylcycloalkyl” include methylcyclopropyl,ethylcyclopentyl, and other straight-chain or branched alkyl groupsbonded to cycloalkyl moiety. The term “alkoxycycloalkyl” denotes alkoxysubstitution on a cycloalkyl moiety. Examples of “alkoxycycloalkyl”include methoxycyclopropyl, ethoxycyclopentyl, and other straight-chainor branched alkoxy groups bonded to a cycloalkyl moiety.“Cycloalkylalkoxy” denotes cycloalkylalkyl linked through an oxygen atomattached to the alkyl chain. Examples of “cycloalkylalkoxy” includecyclopropylmethoxy, cyclopentylethoxy, and other cycloalkyl moietiesbonded to straight-chain or branched alkoxy groups. Examples of“cyanocycloalkyl” include 4-cyanocyclohexyl and 3-cyanocyclopentyl.“Cycloalkenyl” includes groups such as cyclopentenyl and cyclohexenyl aswell as groups with more than one double bond such as 1,3- and1,4-cyclohexadienyl.

The term “halogen”, either alone or in compound words such as“haloalkyl”, or when used in descriptions such as “alkyl substitutedwith halogen” includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, or when used indescriptions such as “alkyl substituted with halogen” said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” or “alkyl substituted withhalogen” include F₃C—, ClCH₂—, CF₃CH₂— and CF₃CCl₂—. The terms“halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, haloalkylsulfinyl,haloalkylsulfonyl, “haloalkenyloxy”, “haloalkynyloxy” “haloalkenyl”,“haloalkynyl”, “haloalkoxyalkyl”, “haloalkoxyalkoxy”“haloalkoxyhaloalkoxy”, “haloalkoxyhaloalkyl”, “halo alkylamino”,“haloalkylaminoalkyl” “halocycloalkoxy”, “halocycloalkoxyalkyl”,“halocycloalkylalkyl”, “halocycloalkenyl”, “halocycloalkenyloxy”,“halocycloalkenyloxy”, “halocycloalkenyloxyalkyl”, “alkoxyhaloalkoxy”,alkoxyhaloalkyl, haloalkylcarbonyloxy, and the like, are definedanalogously to the term “haloalkyl”. Examples of “haloalkoxy” includeCF₃O—, CCl₃CH₂O—, HCF₂CH₂CH₂O— and CF₃CH₂O—. Examples of “haloalkylthio”include CCl₃S—, CF₃S—, CCl₃CH₂S— and ClCH₂CH₂CH₂S—. Examples of“haloalkylsulfinyl” include CF₃S(O)—, CCl₃S(O)—, CF₃CH₂S(O)— andCF₃CF₂S(O)—. Examples of “haloalkylsulfonyl” include CF₃S(O)₂—,CCl₃S(O)₂—, CF₃CH₂S(O)₂— and CF₃CF₂S(O)₂—. Examples of “haloalkenyl”include (Cl)₂C═CHCH₂— and CF₃CH₂CH═CHCH₂—. Examples of “haloalkynyl”include HC≡CCHCl—, CF₃C≡C—, CCl₃C≡C— and FCH₂C≡CCH₂—. Examples of“haloalkoxyalkoxy” include CF₃OCH₂O—, ClCH₂CH₂OCH₂CH₂O—, Cl₃CCH₂OCH₂O—as well as branched alkyl derivatives. Examples of “haloalkylamino”include CF₃(CH₃)CHNH, (CF₃)₂CHNH and CH₂ClCH₂NH. The term “halodialkyl”,either alone or in compound words such as “halodialkylamino”, means atleast one of the two alkyl groups is substituted with at least onehalogen atom, and independently each halogenated alkyl group may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “halodialkylamino” include (BrCH₂CH₂)₂N andBrCH₂CH₂(ClCH₂CH₂)N.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moietiesbonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH₃C(═O)—,CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. Examples of “alkoxycarbonyl” includeCH₃OC(═O)—, CH₃CH₂OC(═O)—, CH₃CH₂CH₂OC(═O)—, (CH₃)₂CHOC(═O)— and thedifferent butoxy- or pentoxycarbonyl isomers. The terms“haloalkylcarbonyl” “haloalkoxycarbonyl”, “alkoxyalkylcarbonyl”,“cycloalkoxycarbonyl”, “cycloalkylalkoxycarbonyl”,“cycloalkylaminocarbonyl” are defined analogously.

The term “alkoxycarbonylamino” denotes a straight-chain or branchedalkoxy moieties bonded to a C(═O) moiety of carbonylamino group.Examples of “alkoxycarbonylamino” include CH₃OC(═O)NH— andCH₃CH₂OC(═O)NH—. Examples of “alkylaminocarbonyl” include CH₃NHC(═O),CH₃CH₂NHC(═O), CH₃CH₂CH₂NHC(═O), (CH₃)₂CHNHC(═O) and the differentbutylamino- or pentylaminocarbonyl isomers. Examples of“dialkylaminocarbonyl” include (CH₃)₂NC(═O), (CH₃CH₂)₂NC(═O),CH₃CH₂(CH₃)NC(═O), (CH₃)₂CH(CH₃)NC(═O) and CH₃CH₂CH₂(CH₃)NC(═O). Theterm “alkylcarbonyloxy” denotes straight-chain or branched alkyl bondedto a C(═O)O moiety. Examples of “alkylcarbonyloxy” include CH₃CH₂C(═O)Oand (CH₃)₂CHC(═O)O. The term “alkylcarbonylalkoxy” denotes alkylcarbonylbonded to an alkoxy moiety. Examples of “alkylcarbonylalkoxy” includeCH₃C(═O)CH₂CH₂O and CH₃CH₂C(═O)CH₂O. Examples of “alkoxycarbonyloxy”include CH₃CH₂CH₂OC(═O)O and (CH₃)₂CHOC(═O)O. The term“cycloalkylcarbonyloxy” denotes a cycloalkylcarbonyl group bonded tooxygen. Examples of “cycloalkylcarbonyloxy” include c-Pr—C(O)O— andc-hexyl-C(O)O—.

“Alkylsulfonylamino” denotes an NH radical substituted withalkylsulfonyl. Examples of “alkylsulfonylamino” include CH₃CH₂S(═O)₂NH—and (CH₃)₂CHS(═O)₂NH—. The term “alkylsulfonyloxy” denotes analkylsulfonyl group bonded to an oxygen atom. Examples of“alkylsulfonyloxy” include CH₃S(═O)₂O—, CH₃CH₂S(═O)₂O—,CH₃CH₂CH₂S(═O)₂O—, (CH₃)₂CHS(═O)₂O—, and the different butylsulfonyloxy,pentylsulfonyloxy and hexylsulfonyloxy isomers.

The term “cycloalkoxyalkyl” denotes cycloalkoxy substitution on an alkylmoiety. Examples of “cycloalkoxyalkyl” include cyclopropyloxymethyl,cyclopentyloxyethyl, and other cycloalkoxy moieties bonded tostraight-chain or branched alkyl groups. The term “cycloalkylthio”denotes cycloalkyl attached to and linked through a sulfur atom such ascyclopropylthio and cyclopentylthio; “cycloalkylsulfonyl” includes thecorresponding sulfones. “Alkylcycloalkylalkyl” denotes an alkyl groupsubstituted with alkylcycloalkyl. Examples of “alkylcycloalkylalkyl”include 1-, 2-, 3- or 4-methyl or -ethyl cyclohexylmethyl. The term“cycloalkoxyalkoxyalkyl” denotes a cycloalkoxy moiety attached to analkoxyalkyl group. Examples of the term “cycloalkoxyalkoxyalkyl” include(tetrahydrofuran-2-yl)CH₂OCH₂—, (tetrahydrofuran-3-yl)CH₂CH₂OCH₂— or(oxiran-2-yl)CH₂OCH₂CH₂—. The term “cycloalkylcycloalkyl” denotescycloalkyl substitution on another cycloalkyl ring, wherein eachcycloalkyl ring independently has from 3 to 7 carbon atom ring members.Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (such as1,1′-bicyclopropyl-1-yl, 1,1′-bicyclopropyl-2-yl), cyclohexylcyclopentyl(such as 4-cyclopentylcyclohexyl) and cyclohexylcyclohexyl (such as1,1′-bicyclohexyl-1-yl), and the different cis- andtrans-cycloalkylcycloalkyl isomers, (such as(1R,2S)-1,1′-bicyclopropyl-2-yl and (1R,2R)-1,1′-bicyclopropyl-2-yl).

“Dialkoxyalkyl” denotes two independent alkoxy groups substituted onsame carbon of the alkyl group. Examples of “dialkoxyalkyl” include(CH₃O)₂CH— and CH₃CH₂O(CH₃O)CH—. “Cycloalkylamino” denotes an NH radicalsubstituted with cycloalkyl. Examples of “cycloalkylamino” includecyclopropylamino and cyclohexylamino. “Cycloalkyl(alkyl)amino” means acycloalkylamino group where the hydrogen atom is replaced by an alkylradical. Examples of “cycloalkyl(alkyl)amino” include groups such ascyclopropyl(methyl)amino, cyclobutyl(butyl)amino,cyclopentyl(propyl)amino, cyclohexyl(methyl)amino and the like. The term“cycloalkylaminoalkyl” denotes cycloalkylamino substitution on an alkylgroup. Examples of “cycloalkylaminoalkyl” includecyclopropylaminomethyl, cyclopentylaminoethyl, and other cycloalkylaminomoieties bonded to straight-chain or branched alkyl groups.

“Cycloalkylcarbonyl” denotes cycloalkyl bonded to a C(═O) groupincluding, for example, cyclopropylcarbonyl and cyclopentylcarbonyl. Theterm “cycloalkoxycarbonyl” means cycloalkoxy bonded to a C(═O) group,for example, cyclopropyloxycarbonyl and cyclopentyloxycarbonyl.“Cycloalkylaminocarbonyl” denotes cycloalkylamino bonded to a C(═O)group, for example, cyclopentylaminocarbonyl andcyclohexylaminocarbonyl. “Cycloalkylalkoxycarbonyl” denotescycloalkylalkoxy bonded to a C(═O) group. Examples of“cycloalkylalkoxycarbonyl” include cyclopropylethoxycarbonyl andcyclopentylmethoxycarbonyl. “Cycloalkylcarbonyloxy” denotescycloalkylcarbonyl attached to and linked through an oxygen atom.Examples of “cycloalkylcarbonyloxy” include cyclohexylcarbonyloxy andcyclopentylcarbonyloxy.

The term “cycloalkenylalkyl” denotes cycloalkenyl substitution on analkyl moiety. Examples of “cycloalkenylalkyl” includecyclobutenylmethyl, cyclopentenylethyl, and other cycloalkenyl moietiesbonded to straight-chain or branched alkyl groups. The term“cycloalkenyloxy” denotes cycloalkenyl linked through an oxygen atomsuch as cyclopentenyloxy and cyclohexenyloxy. The term“cycloalkenyloxyalkyl” denotes cycloalkenyloxy substitution on an alkylmoiety. Examples of “cycloalkenyloxyalkyl” includecyclobutenyloxymethyl, cyclopentenyloxyethyl, and other cycloalkenyloxymoieties bonded to straight-chain or branched alkyl groups.

The term “alkylaminosulfonyl” denotes a straight-chain or branchedalkylamino moiety bonded to a sulfonyl group. Examples of an“alkylaminosulfonyl” group include CH₃NHS(O)₂— or CH₃CH₂CH₂NHS(O)₂—. Theterm “dialkylaminosulfonyl” denotes a straight-chain or brancheddialkylamino moiety bonded to a sulfonyl group. Examples of a“dialkylaminosulfonyl” group include (CH₃)₂NS(O)₂— or(CH₃CH₂CH₂)₂NS(O)₂—.

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 14. Forexample, C₁-C₄ alkylsulfonyl designates methylsulfonyl throughbutylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂—; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃)—, CH₃OCH₂CH₂— or CH₃CH₂OCH₂—; andC₄ alkoxyalkyl designates the various isomers of an alkyl groupsubstituted with an alkoxy group containing a total of four carbonatoms, examples including CH₃CH₂CH₂OCH₂— and CH₃CH₂OCH₂CH₂—.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents, e.g., (R^(v))_(r), r is 1, 2, 3, 4 or 5in U-1 of Exhibit 2. When a group contains a substituent which can behydrogen, for example R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹²,R¹³, R¹⁴, R¹⁵, R¹⁸, R¹⁹ or R²⁰, then when this substituent is taken ashydrogen, it is recognized that this is equivalent to said group beingunsubstituted. When a variable group is shown to be optionally attachedto a position, for example (R^(v))_(r) in Q-29 of Exhibit 1 thenhydrogen may be at the position even if not recited in the variablegroup definition. When one or more positions on a group are said to be“not substituted” or “unsubstituted”, then hydrogen atoms are attachedto take up any free valency.

Unless otherwise indicated, a “ring” or “ring system” as a component ofFormula 1 (e.g., substituent G) is carbocyclic or heterocyclic. The term“ring system” denotes two or more fused rings. The terms “bicyclic ringsystem” and “fused bicyclic ring system” denote a ring system consistingof two fused rings, in which either ring can be saturated, partiallyunsaturated, or fully unsaturated unless otherwise indicated. The term“ring member” refers to an atom or other moiety (e.g., C(═O), C(═S),S(O) or S(O)₂) forming the backbone of a ring or ring system.

The terms “carbocyclic ring”, “carbocycle” or “carbocyclic ring system”denote a ring or ring system wherein the atoms forming the ring backboneare selected only from carbon. Unless otherwise indicated, a carbocyclicring can be a saturated, partially unsaturated, or fully unsaturatedring. When a fully unsaturated carbocyclic ring satisfies Hückel's rule,then said ring is also called an “aromatic ring”. “Saturatedcarbocyclic” refers to a ring having a backbone consisting of carbonatoms linked to one another by single bonds; unless otherwise specified,the remaining carbon valences are occupied by hydrogen atoms.

The terms “heterocyclic ring”, “heterocycle” or “heterocyclic ringsystem” denote a ring or ring system in which at least one atom formingthe ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur.Typically a heterocyclic ring contains no more than 4 nitrogens, no morethan 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, aheterocyclic ring can be a saturated, partially unsaturated, or fullyunsaturated ring. When a fully unsaturated heterocyclic ring satisfiesHückel's rule, then said ring is also called a “heteroaromatic ring” or“aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclicrings and ring systems can be attached through any available carbon ornitrogen by replacement of a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in thesame plane and has a p-orbital perpendicular to the ring plane, and that(4n+2) π electrons, where n is a positive integer, are associated withthe ring to comply with Hückel's rule. The term “aromatic ring system”denotes a carbocyclic or heterocyclic ring system in which at least onering of the ring system is aromatic. The term “aromatic carbocyclic ringsystem” denotes a carbocyclic ring system in which at least one ring ofthe ring system is aromatic. The term “aromatic heterocyclic ringsystem” denotes a heterocyclic ring system in which at least one ring ofthe ring system is aromatic. The term “nonaromatic ring system” denotesa carbocyclic or heterocyclic ring system that may be fully saturated,as well as partially or fully unsaturated, provided that none of therings in the ring system are aromatic. The term “nonaromatic carbocyclicring system” denotes a carbocylcic ring system in which no ring in thering system is aromatic. The term “nonaromatic heterocyclic ring system”denotes a heterocyclic ring system in which no ring in the ring systemis aromatic.

As used herein, the following definitions shall apply unless otherwiseindicated. The term “optionally substituted” is used interchangeablywith the phrase “substituted or unsubstituted” or with the term“(un)substituted.” Unless otherwise indicated, an optionally substitutedgroup may have a substituent at each substitutable position of thegroup, and each substitution is independent of the other.

When G is a 5- or 6-membered nitrogen-containing heterocyclic ring, itmay be attached to the remainder of Formula 1 through any availablecarbon or nitrogen ring atom, unless otherwise described. When G is(among others) a 5- or 6-membered heterocyclic ring it may be saturatedor unsaturated, optionally substituted with one or more substituentsselected from a group of substituents as defined in the Summary of theInvention. Examples of a 5- or 6-membered unsaturated aromaticheterocyclic ring optionally substituted with from one or moresubstituents include the rings Q-1 through Q-60 illustrated in Exhibit 1wherein R^(v) is any substituent as defined in the Summary of theInvention for R²¹ on carbon ring members or R²² on nitrogen ringmembers, and r is an integer from 0 to 4, limited by the number ofavailable positions on each Q group. As Q-29, Q-30, Q-36, Q-37, Q-38,Q-39, Q-40, Q-41, Q-42 and Q-43 have only one available position, forthese Q groups r is limited to the integers 0 or 1, and r being 0 meansthat the Q group is unsubstituted and a hydrogen is present at theposition indicated by (R^(v))_(r).

Note that when G is a 5- or 6-membered saturated or unsaturatednon-aromatic heterocyclic ring optionally substituted with one or moresubstituents selected from the group of substituents as defined in theSummary of the Invention for R²¹ one or two carbon ring members of theheterocycle can optionally be in the oxidized form of a carbonyl moiety.

Examples of a 5- or 6-membered saturated or non-aromatic unsaturatedheterocyclic ring include the rings U-1 through U-36 as illustrated inExhibit 2. Note that when the attachment point on the U group isillustrated as floating, the U group can be attached to the remainder ofFormula 1 through any available carbon or nitrogen of the U group byreplacement of a hydrogen atom. The optional substituents correspondingto R^(v) can be attached to any available carbon or nitrogen byreplacing a hydrogen atom. For these U rings, r is typically an integerfrom 0 to 4, limited by the number of available positions on each Ugroup.

Note that when G comprises a ring selected from U-29 through U-36, U² isselected from O, S or N. Note that when U² is N, the nitrogen atom cancomplete its valence by substitution with either H or the substituentscorresponding to R^(v) as defined in the Summary of the Invention for U(i.e. R²²).

As noted above, G can be (among others) an 8-, 9- or 10-membered fusedbicyclic ring system optionally substituted with one or moresubstituents selected from a group of substituents as defined in theSummary of the Invention (i.e. R²¹). Examples of 8-, 9- or 10-memberedfused bicyclic ring system optionally substituted with from one or moresubstituents include the rings Q-81 through Q-123 illustrated in Exhibit3 wherein R^(v) is any substituent as defined in the Summary of theInvention for G (i.e. R²¹ or R²²), and r is typically an integer from 0to 4.

Although R^(v) groups are shown in the structures Q-1 through Q-60 andQ-81 through Q-123, it is noted that they do not need to be presentsince they are optional substituents. The nitrogen atoms that requiresubstitution to fill their valence are substituted with H or R^(v). Notethat when the attachment point between (R^(v))_(r) and the Q group isillustrated as floating, (R^(v))_(r) can be attached to any availablecarbon atom or nitrogen atom of the Q group. Note that when theattachment point on the Q group is illustrated as floating, the Q groupcan be attached to the remainder of Formula 1 through any availablecarbon or nitrogen of the Q group by replacement of a hydrogen atom.Note that some Q groups can only be substituted with less than 4 R^(v)groups (e.g., Q-1 through Q-5, Q-7 through Q-48, and Q-52 through Q-60).

As noted in the Summary of the Invention, R¹ and R² are taken togetheralong with the atoms to which they are attached to make a 5-, 6- or7-membered unsaturated, partially unsaturated or fully unsaturated ringalong with members consisting of up to 2 oxygen atoms, 2 nitrogen atomsor 2 sulfur atoms or up to two —S(O)—, —S(O)₂—, —C(O)— groups. Besidesthe possibility of R¹ and R² being separate substituents, they may alsobe connected to form a ring fused to the ring to which they areattached. The fused ring can be a 5-, 6- or 7-membered ring including asring members the two atoms shared with the ring to which thesubstituents are attached. The other 3, 4 or 5 ring members of the fusedring are provided by R¹ and R² substituents taken together. These otherring members can include up to 5 carbon atoms (as allowed by the ringsize) and optionally up to 3 heteroatoms selected from up to 2 O, up to2 S and up to 3 N. The fused ring is optionally substituted with up to 3substituents as noted in the Summary of the Invention. Exhibit 4provides, as illustrative examples, rings formed by R¹ and R² takentogether. As these rings are fused with a ring of Formula 1, a portionof the Formula 1 ring is shown and the truncated lines represent thering bonds of the Formula 1 ring. The rings depicted are fused to thetwo adjacent atoms of a ring as shown in Formula 1. The optionalsubstituents (R^(v))_(r), are independently selected from the groupconsisting of halogen, cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl and C₂-C₈ alkoxyalkyl; and phenyloptionally substituted with up to 5 substituents selected from cyano,nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy; oncarbon atom ring members. The optional substituents (R^(v))_(r), areindependently selected from the group consisting of H and C₁-C₆ alkyl;and phenyl optionally substituted with up to 5 substituents selectedfrom cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆haloalkoxy; on nitrogen ring members. Substituents are limited by thenumber of available positions on each T-ring. When the attachment pointbetween (R^(v))_(r) and the T-ring is illustrated as floating, R^(v) maybe bonded to any available T-ring carbon or nitrogen atom (asapplicable). One skilled in the art recognizes that while r is nominallyan integer from 0 to 3, some of the rings shown in Exhibit 4 have lessthan 3 available positions, and for these groups r is limited to thenumber of available positions. When “r” is 0 this means the ring isunsubstituted and hydrogen atoms are present at all available positions.If r is 0 and (R^(v))_(r) is shown attached to a particular atom, thenhydrogen is attached to that atom. The nitrogen atoms that requiresubstitution to fill their valence are substituted with H or R^(v).Furthermore, one skilled in the art recognizes that some of the ringsshown in Exhibit 4 can form tautomers, and the particular tautomerdepicted is representative of all the possible tautomers.

A wide variety of synthetic methods are known in the art to enablepreparation of aromatic and nonaromatic heterocyclic rings and ringsystems; for extensive reviews see the eight volume set of ComprehensiveHeterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief,Pergamon Press, Oxford, 1984 and the twelve volume set of ComprehensiveHeterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. One skilled in the art will appreciate that onestereoisomer may be more active and/or may exhibit beneficial effectswhen enriched relative to the other stereoisomer(s) or when separatedfrom the other stereoisomer(s). Additionally, the skilled artisan knowshow to separate, enrich, and/or to selectively prepare saidstereoisomers. The compounds of the invention may be present as amixture of stereoisomers, individual stereoisomers or as an opticallyactive form.

One skilled in the art will recognize that when A is A-1, A-2 or A-3,and the R³ variable is hydroxy or O⁻M⁺, then the resulting compound ofFormula 1 can exist in either the “triketone” tautomer or the “di-ketoenol” tautomer. Likewise, when A is A-1, A-2 or A-3, and the R³ variableis —SH, the resulting compound of Formula 1 can exist in either the the“di-keto thioketo” tautomer or the “di-keto thioenol” tautomer. In anyof these cases and for the purposes of this invention both tautomericcombinations represent fully functional species of the presentinvention. For example, named species using the phrase“2-(1,3-cyclohexanedione)” is synonomous with the term“3-oxo-1-cyclohexen-1-yl”.

Compounds of Formula 1 typically exist in more than one form, andFormula 1 thus include all crystalline and non-crystalline forms of thecompounds they represent. Non-crystalline forms include embodimentswhich are solids such as waxes and gums as well as embodiments which areliquids such as solutions and melts. Crystalline forms includeembodiments which represent essentially a single crystal type andembodiments which represent a mixture of polymorphs (i.e. differentcrystalline types). The term “polymorph” refers to a particularcrystalline form of a chemical compound that can crystallize indifferent crystalline forms, these forms having different arrangementsand/or conformations of the molecules in the crystal lattice. Althoughpolymorphs can have the same chemical composition, they can also differin composition due the presence or absence of co-crystallized water orother molecules, which can be weakly or strongly bound in the lattice.Polymorphs can differ in such chemical, physical and biologicalproperties as crystal shape, density, hardness, color, chemicalstability, melting point, hygroscopicity, suspensibility, dissolutionrate and biological availability. One skilled in the art will appreciatethat a polymorph of a compound of Formula 1 can exhibit beneficialeffects (e.g., suitability for preparation of useful formulations,improved biological performance) relative to another polymorph or amixture of polymorphs of the same compound of Formula 1. Preparation andisolation of a particular polymorph of a compound of Formula 1 can beachieved by methods known to those skilled in the art including, forexample, crystallization using selected solvents and temperatures.

One skilled in the art will appreciate that not all nitrogen-containingheterocycles can form N-oxides since the nitrogen requires an availablelone pair for oxidation to the oxide; one skilled in the art willrecognize those nitrogen-containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and m-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding nonsalt forms, salts share thebiological utility of the nonsalt forms. Thus a wide variety of salts ofa compound of Formula 1 are useful for control of undesired vegetation(i.e. are agriculturally suitable). The salts of a compound of Formula 1include acid-addition salts with inorganic or organic acids such ashydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic,butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic,tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula1 contains an acidic moiety such as a carboxylic acid or phenol, saltsalso include those formed with organic or inorganic bases such aspyridine, triethylamine or ammonia, or amides, hydrides, hydroxides orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium.Accordingly, the present invention comprises compounds selected fromFormula 1, N-oxides and agriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of theInvention also include (where Formula 1 as used in the followingEmbodiments includes N-oxides and salts thereof):

Embodiment 1

A compound of Formula 1 wherein A is A-1, A-3, A-4, A-5 or A-6.

Embodiment 2

A compound of Embodiment 1 wherein A is A-1, A-3, A-5 or A-6.

Embodiment 3

A compound of Embodiment 2 wherein A is A-1, A-3 or A-5.

Embodiment 4

A compound of Embodiment 3 wherein A is A-1 or A-3.

Embodiment 5

A compound of Embodiment 4 wherein A is A-1.

Embodiment 6

A compound of Embodiment 4 wherein A is A-3.

Embodiment 7

A compound of Formula 1 or any one of Embodiments 1 through 5 wherein Ais other than A-1.

Embodiment 8

A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B¹is C-1.

Embodiment 9

A compound of Formula 1 or any one of Embodiments 1 through 7 wherein B¹is C-2.

Embodiment 10

A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B²is C-3.

Embodiment 11

A compound of Formula 1 or any one of Embodiments 1 through 9 wherein B²is C-4.

Embodiment 12

A compound of Formula 1 or any one of Embodiments 1 through 11 whereinB³ is C-1.

Embodiment 13

A compound of Formula 1 or any one of Embodiments 1 through 11 whereinB³ is C-2.

Embodiment 14

A compound of Formula 1 or any one of Embodiments 1 through 13 whereinR¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),—W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionallysubstituted on ring members with up to five substituents selected fromR²¹; or -G or —W²G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN,—C(═O)NHOH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₁₀ alkyl, C₂-C₁₀alkenyl, C₂-C₁₀ alkynyl, C₁-C₁₀ haloalkyl, C₂-C₁₀ haloalkenyl, C₂-C₁₂haloalkynyl, C₃-C₁₂ cycloalkyl, C₃-C₁₂ halocycloalkyl, C₄-C₁₄alkylcycloalkyl, C₄-C₁₄ cycloalkylalkyl, C₆-C₁₈ cycloalkylcycloalkyl,C₄-C₁₄ halocycloalkylalkyl, C₅-C₁₆ alkylcycloalkylalkyl, C₃-C₁₂cycloalkenyl, C₃-C₁₂ halocycloalkenyl, C₂-C₁₂ alkoxyalkyl, C₃-C₁₂alkoxyalkenyl, C₄-C₁₄ alkylcycloalkyl, C₄-C₁₄ alkoxycycloalkyl, C₄-C₁₄cycloalkoxyalkyl, C₅-C₁₄ cycloalkoxyalkoxyalkyl, C₃-C₁₄alkoxyalkoxyalkyl, C₂-C₁₂ alkylthioalkyl, C₂-C₁₂ alkylsulfinylalkyl,C₂-C₁₂ alkylsulfonylalkyl, C₂-C₁₂ alkylaminoalkyl, C₃-C₁₄dialkylaminoalkyl, C₂-C₁₂ haloalkylaminoalkyl, C₄-C₁₄cycloalkylaminoalkyl, C₂-C₁₂ alkylcarbonyl, C₂-C₁₂ haloalkylcarbonyl,C₄-C₁₄ cycloalkylcarbonyl, C₂-C₁₂ alkoxycarbonyl, C₄-C₁₆cycloalkoxycarbonyl, C₅-C₁₄ cycloalkylalkoxycarbonyl, C₂-C₁₂alkylaminocarbonyl, C₃-C₁₄ dialkylaminocarbonyl, C₄-C₁₄cycloalkylaminocarbonyl, C₂-C₉ cyanoalkyl, C₁-C₁₀ hydroxyalkyl, C₄-C₁₄cycloalkenylalkyl, C₂-C₁₂ haloalkoxyalkyl, C₂-C₁₂ alkoxyhaloalkyl,C₂-C₁₂ haloalkoxyhaloalkyl, C₄-C₁₄ halocycloalkoxyalkyl, C₄-C₁₄cycloalkenyloxyalkyl, C₄-C₁₄ halocycloalkenyloxyalkyl, C₃-C₁₄dialkoxyalkyl, C₃-C₁₄ alkoxyalkylcarbonyl, C₃-C₁₄ alkoxycarbonylalkyl orC₂-C₁₂ haloalkoxycarbonyl.

Embodiment 15

A compound of Formula 1 or any one of Embodiments 1 through 14 whereinR¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),—W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionallysubstituted on ring members with up to five substituents selected fromR²¹; or -G or —W²G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN,—C(═O)NHOH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₄-C₁₀cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl,C₃-C₁₀ dialkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀cycloalkylaminoalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl,C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₄-C₁₀cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀dialkoxyalkyl, C₃-C₁₀ alkoxyalkylcarbonyl, C₃-C₁₀ alkoxycarbonylalkyl orC₂-C₈ haloalkoxycarbonyl.

Embodiment 16

A compound of Embodiment 15 wherein R¹ is phenyl, —W¹(phenyl),—W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl),each optionally substituted on ring members with up to five substituentsselected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl,C₂-C₈ alkylthioalkyl or C₂-C₈ alkylsulfonylalkyl.

Embodiment 17

A compound of Embodiment 16 wherein R¹ is phenyl or —W¹(phenyl), eachoptionally substituted on ring members with up to two substituentsselected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀alkylcycloalkyl or C₄-C₁₀ alkoxycycloalkyl.

Embodiment 18

A compound of Embodiment 17 wherein R¹ is phenyl, 2-fluorophenyl,3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl,3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl,3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl,4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 19

A compound of Embodiment 18 wherein R¹ is phenyl, 4-ethylphenyl,4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl,3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or5-chloro-2-methylphenyl.

Embodiment 20

A compound of Embodiment 19 wherein R¹ is phenyl, 3,4-dimethoxyphenyl or5-chloro-2-methylphenyl.

Embodiment 21

A compound of Embodiment 20 wherein R¹ is phenyl.

Embodiment 22

A compound of Embodiment 19 wherein R¹ is 3,4-dimethoxyphenyl.

Embodiment 23

A compound of Embodiment 19 wherein R¹ is 5-chloro-2-methylphenyl.

Embodiment 24

A compound of Formula 1 or any one of Embodiments 1 through 21 whereinR¹ is other than phenyl.

Embodiment 25

A compound of Embodiment 17 wherein R¹ is -G or —W²G; C₁-C₆ alkyl, C₃-C₈cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 26

A compound of Embodiment 25 wherein R¹ is -G or —W²G.

Embodiment 27

A compound of Embodiment 26 wherein R¹ is C₁-C₆ alkyl, C₃-C₈ cycloalkyl,or C₂-C₈ alkoxyalkyl.

Embodiment 28

A compound of Embodiment 27 wherein R¹ is n-Pr, i-Pr, n-Bu, c-hexyl,c-heptyl, —CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or —CH₂CH₂OCH₂CH₃.

Embodiment 29

A compound of Embodiment 28 wherein R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or—CH₂CH₂CH₂OCH₃.

Embodiment 29a

A compound of Embodiment 29 wherein R¹ is n-Pr or —CH₂CH₂OCH₃.

Embodiment 29b

A compound of Embodiment 29 wherein R¹ is c-hexyl.

Embodiment 30

A compound of Formula 1 or any one of Embodiments 1 through 17 whereinW¹ is C₁-C₆ alkylene.

Embodiment 31

A compound of Embodiment 30 wherein W¹ is —CH₂—.

Embodiment 32

A compound of Formula 1 or any one of Embodiments 1 through 17, 25 or 26wherein W² is —CH₂—.

Embodiment 33

A compound of Formula 1 or any one of Embodiments 1 through 32 whereinR² is phenyl or —W³(phenyl), each optionally substituted on ring memberswith up to five substituents selected from R²¹; or -G; C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀alkoxyalkenyl, C₄-C₁₀ cycloalkoxyalkyl, C₄-C₁₀ cycloalkoxylalkoxyalkyl,C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl,C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl,C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀dialkoxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀cycloalkylcarbonyloxy, C₃-C₁₀ alkylcarbonylalkoxy, C₁-C₆ alkylthio,C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈cycloalkylsulfonyl, C₃-C₈ trialkylsilyl, C₃-C₈ cycloalkenyloxy, C₃-C₈halocycloalkenyloxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyhaloalkoxy,C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₁₀ alkoxycarbonylalkoxy, C₂-C₈alkyl(thiocarbonyl)oxy, C₃-C₈ cycloalkylsulfinyl or C₃-C₁₀halotrialkylsilyl.

Embodiment 34

A compound of Embodiment 33 wherein R² is phenyl or —W³(phenyl), eachoptionally substituted on ring members with up to two substituentsselected from R²¹; or -G or; or C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 35

A compound of Embodiment 34 wherein R² is phenyl optionally substitutedon ring members with up to two substituents selected from R²¹; or -G; orC₁-C₆ alkyl, C₃-C₈ cycloalkyl.

Embodiment 36

A compound of Embodiment 35 wherein R² is phenyl, 2-methylphenyl,3-methylphenyl, 4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl.

Embodiment 36a

A compound of Embodiment 35 wherein R² is phenyl, 3-bromophenyl,3-chlorophenyl, or 2-methylphenyl.

Embodiment 37

A compound of Embodiment 35 wherein R² is phenyl.

Embodiment 38

A compound of Formula 1 or any one of Embodiments 1 through 36 whereinR² is other than phenyl.

Embodiment 39

A compound of Embodiment 35 wherein R² is 3-thienyl or 2-thienyl.

Embodiment 40

A compound of Embodiment 35 wherein R² is n-propyl, n-butyl, orcyclopropyl.

Embodiment 41

A compound of Formula 1 or any one of Embodiments 1 through 13 whereinR¹ and R² are taken together along with the atoms to which they areattached to make a 6- or 7-membered unsaturated, partially unsaturatedor fully unsaturated ring along with members consisting of up to 2oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two —S(O)—,—S(O)₂—, —C(O)— groups optionally substituted on carbon atom ringmembers selected from halogen, cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl and C₂-C₈ alkoxyalkyl; andphenyl optionally substituted with up to 5 substituents selected fromcyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy;and optionally substituted on nitrogen ring members selected from H andC₁-C₆ alkyl; and phenyl optionally substituted with up to 5 substituentsselected from cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆haloalkoxy.

Embodiment 42

A compound of Embodiment 41 wherein R¹ and R² are taken together alongwith the atoms to which they are attached to make a 6- or 7-memberedunsaturated, partially unsaturated or fully unsaturated ring along withmembers consisting of up to 1 oxygen atoms, 1 nitrogen atoms or 1 sulfuratoms or up to one —S(O)—, —S(O)₂—, —C(O)— groups optionally substitutedon carbon atom ring members selected from halogen, cyano, C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl andC₂-C₈ alkoxyalkyl; and optionally substituted on nitrogen ring membersselected from H and C₁-C₆ alkyl.

Embodiment 43

A compound of Embodiment 42 wherein R¹ and R² are taken together alongwith the atoms to which they are attached to make a 7-membered partiallyunsaturated ring optionally substituted with halogen, cyano, C₁-C₆alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkylor C₂-C₈ alkoxyalkyl on carbon atom ring members.

Embodiment 44

A compound of Embodiment 43 wherein R¹ and R² are taken together alongwith the atoms to which they are attached to make an unsubstituted7-membered partially unsaturated ring.

Embodiment 45

A compound of Formula 1 or any one of Embodiments 1 through 34 whereinW³ is —CH₂—.

Embodiment 46

A compound of Formula 1 or any one of Embodiments 1 through 32 whereinW⁴ is —CH₂—.

Embodiment 47

A compound of Formula 1 or any one of Embodiments 1 through 46 whereinR³ is hydroxy, —O⁻M⁺, C₂-C₈ alkylcarbonyloxy, C₂-C₈haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy or C₃-C₁₀alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy,phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, eachoptionally substituted on ring members with up to two substituentsselected from R²¹.

Embodiment 48

A compound of Embodiment 47 wherein R³ is hydroxy, —O⁻M⁺ or C₂-C₈alkylcarbonyloxy; or phenylsulfonyloxy optionally substituted with up totwo substituents selected from R²¹.

Embodiment 49

A compound of Embodiment 48 wherein M⁺ is a sodium or potassium metalcation.

Embodiment 50

A compound of Embodiment 49 wherein R³ is hydroxy or C₂-C₈alkylcarbonyloxy.

Embodiment 51

A compound of Embodiment 50 wherein R³ is hydroxy or —OC(═O)CH₂CH(CH₃)₂.

Embodiment 52

A compound of Formula 1 or any one of Embodiments 1, 7 and 14 through 51wherein R⁴, R⁵, R⁶ and R⁷ are each independently H, or C₁-C₆ alkyl.

Embodiment 53

A compound of Formula 1 or any one of Embodiments 1, 7 and 14 through 52wherein R⁸ is C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 54

A compound of Embodiment 53 wherein R⁸ is CH₃, CH₂CH₃ or cyclopropyl.

Embodiment 55

A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14through 51 wherein R⁹ is C₁-C₆ alkyl.

Embodiment 56

A compound of Embodiment 55 wherein R⁹ is CH₂CH₃.

Embodiment 57

A compound of Formula 1 or any one of Embodiments 1 through 3, 7 and 14through 51 wherein R¹⁰ is H, halogen or C₁-C₆ alkyl.

Embodiment 58

A compound of Embodiment 57 wherein R¹⁰ is H or CH₃.

Embodiment 59

A compound of Formula 1 or any one of Embodiments 1, 2, 8, 10 and 12through 51 wherein R¹¹ is H or C₁-C₆ alkyl.

Embodiment 60

A compound of Embodiment 59 wherein R¹¹ is H.

Embodiment 61

A compound of Formula 1 or any one of Embodiments 1, 2, 8, 10 and 12through 51 wherein R¹² is H, halogen, cyano, hydroxy, amino or C₁-C₆alkyl.

Embodiment 62

A compound of Embodiment 61 wherein R¹² is H, halogen, cyano, C₁-C₆alkyl or C₃-C₈ cycloalkyl.

Embodiment 63

A compound of Embodiment 62 wherein R¹² is CH₃, CH₂CH₃ or cyclopropyl.

Embodiment 64

A compound of Formula 1 or any one of Embodiments 7 and 15 through 51wherein R¹³ is H, halogen, cyano or nitro.

Embodiment 65

A compound of Embodiment 64 wherein R¹³ is cyano or nitro.

Embodiment 66

A compound of Formula 1 or any one of Embodiments 1 through 65 whereinwhen instances of R¹⁴ and R¹⁸ are taken alone (i.e. R¹⁴ and R¹⁸ are nottaken together as alkylene or alkenylene), then independently saidinstances of R¹⁴ and R¹⁸ are H or C₁-C₆ alkyl.

Embodiment 67

A compound of Embodiment 66 wherein when instances of R¹⁴ and R¹⁸ aretaken alone, then independently said instances of R¹⁴ and R¹⁸ are H orCH₃.

Embodiment 68

A compound of Embodiment 68 wherein when instances of R¹⁴ and R¹⁸ aretaken alone, then independently said instances of R¹⁴ and R¹⁸ are H.

Embodiment 69

A compound of Formula 1 or any one of Embodiments 1 through 68 whereinwhen instances of R¹⁴ and R¹⁸ are taken together, then said instances ofR¹⁴ and R¹⁸ are taken together as —CH₂CH₂CH₂— or —CH═CHCH₂—.

Embodiment 70

A compound of Formula 1 or any one of Embodiments 1 through 68 whereinall instances of R¹⁴ and R¹⁸ are taken alone.

Embodiment 71

A compound of Formula 1 or any one of Embodiments 1 through 70 whereinindependently each R¹⁵ and R¹⁹ is H or C₁-C₆ alkyl.

Embodiment 72

A compound of Embodiment 71 wherein independently each R¹⁵ and R¹⁹ is Hor CH₃.

Embodiment 73

A compound of Embodiment 72 wherein independently each R¹⁵ and R¹⁹ is H.

Embodiment 73a

A compound of Embodiments 67 and 72 wherein each R¹⁴, R¹⁵, R¹⁸ and R¹⁹is H or CH₃.

Embodiment 73b

A compound of Embodiment 73 wherein each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.

Embodiment 74

A compound of Formula 1 or any one of Embodiments 1 through 73 whereinR²⁰ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl or C₃-C₈ cycloalkyl.

Embodiment 75

A compound of Embodiment 74 wherein R²⁰ is H or CH₃.

Embodiment 76

A compound of Formula 1 or any one of Embodiments 1 through 4, 6, 10, 11and 14 through 51 wherein T is —CH₂CH₂— or —CH═CH—.

Embodiment 77

A compound of Embodiment 76 wherein T is —CH₂CH₂—.

Embodiment 78

A compound of Formula 1 or any one of Embodiments 1 through 17 whereineach G is independently a 5- or 6-membered heterocyclic ring optionallysubstituted with up to five substituents selected from R²¹ on carbonring members and R²² on nitrogen ring members.

Embodiment 79

A compound of Embodiment 78 wherein G is

-   -   r is 0, 1, 2 or 3.

Embodiment 80

A compound of Embodiment 79 wherein G is G-2, G-3, G-9, G-15, G-18, G-19or G-20.

Embodiment 81

A compound of Embodiment 79 wherein when R¹ is G, then G is G-18, G-19or G-20.

Embodiment 82

A compound of Embodiment 81 wherein when R¹ is G, then G is G-19 orG-20.

Embodiment 83

A compound of Embodiment 82 wherein when R¹ is G, then G is G-20.

Embodiment 84

A compound of Embodiment 82 wherein when R¹ is G, then G is G-19.

Embodiment 85

A compound of Embodiment 79 wherein when R² is G, then G is G-2, G-3 orG-15.

Embodiment 86

A compound of Embodiment 84 wherein when R² is G, then G is G-2 or G-3.

Embodiment 87

A compound of Embodiment 84 wherein when R² is G, then G is G-2.

Embodiment 88

A compound of Embodiment 84 wherein when R² is G, then G is G-3.

Embodiment 89

A compound of Formula 1 or any one of Embodiments 1 through 88 whereineach R²¹ is independently halogen, cyano, hydroxy, nitro, —CHO, —SH,C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₃-C₈ cycloalkenyl,C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl,C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₅ cyanoalkyl, C₁-C₆hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆haloalkenyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl or C₃-C₈ cycloalkylsulfonyl.

Embodiment 90

A compound of Embodiment 91 wherein each R²¹ is independently halogen,nitro, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy orC₁-C₆ alkylthio.

Embodiment 91

A compound of Embodiment 92 wherein each R²¹ is independently fluorine,chlorine, bromine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment 92

A compound of Formula 1 or any one of Embodiments 1 through 91 whereineach R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 93

A compound of Embodiment 92 wherein each R²² is independently CH₃ orCH₂CF₃.

This invention also includes a herbicidal mixture comprising (a) acompound of Formula 1 and (b) at least one additional active ingredientselected from (b1) photosystem II inhibitors, (b2) AHAS inhibitors, (b3)ACCase inhibitors, (b4) auxin mimics and (b5) EPSP inhibitors.

Embodiment 94

A herbicidal mixture comprising (a) a compound of Formula 1 and (b) atleast one additional active ingredient selected from (b1), (b2) and(b3).

Embodiment 95

A herbicidal mixture comprising (a) a compound of Formula 1 and (b) atleast one additional active ingredient selected from (b1).

Embodiment 96

A herbicidal mixture of Embodiment 95 comprising (a) a compound ofFormula 1 and (b) one additional active ingredient selected from thegroup consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil,bromoxynil, chlorotoluron, dimethametryn, diuron, hexazinone,isoproturon, metribuzin, pyridate, simazine and terbutryn.

Embodiment 97

A herbicidal mixture of Embodiment 95 comprising (a) a compound ofFormula 1; and (b) bromoxynil.

Embodiment 98

A herbicidal mixture of Embodiment 95 comprising (a) a compound ofFormula 1; and (b) dimethametryn.

Embodiment 99

A herbicidal mixture comprising (a) a compound of Formula 1 and (b)diuron and hexazinone.

Combinations of Embodiments 1-93 are illustrated by:

Embodiment A

A compound of Formula 1 wherein

-   -   A is A-1, A-3, A-4, A-5 or A-6;    -   R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),        —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each        optionally substituted on ring members with up to five        substituents selected from R²¹; or -G or —W²G; or cyano,        hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂,        —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₁₀ alkyl, C₂-C₁₀ alkenyl, C₂-C₁₀        alkynyl, haloalkyl, C₂-C₁₀ haloalkenyl, C₂-C₁₂ haloalkynyl,        C₃-C₁₂ cycloalkyl, C₃-C₁₂ halocycloalkyl, C₄-C₁₄        alkylcycloalkyl, C₄-C₁₄ cycloalkylalkyl, C₆-C₁₈        cycloalkylcycloalkyl, C₄-C₁₄ halocycloalkylalkyl, C₅-C₁₆        alkylcycloalkylalkyl, C₃-C₁₂ cycloalkenyl, C₃-C₁₂        halocycloalkenyl, C₂-C₁₂ alkoxyalkyl, C₃-C₁₂ alkoxyalkenyl,        C₄-C₁₄ alkylcycloalkyl, C₄-C₁₄ alkoxycycloalkyl, C₄-C₁₄        cycloalkoxyalkyl, C₅-C₁₄ cycloalkoxyalkoxyalkyl, C₃-C₁₄        alkoxyalkoxyalkyl, C₂-C₁₂ alkylthioalkyl, C₂-C₁₂        alkylsulfinylalkyl, C₂-C₁₂ alkylsulfonylalkyl, C₂-C₁₂        alkylaminoalkyl, C₃-C₁₄ dialkylaminoalkyl, C₂-C₁₂        haloalkylaminoalkyl, C₄-C₁₄ cycloalkylaminoalkyl, C₂-C₁₂        alkylcarbonyl, C₂-C₁₂ haloalkylcarbonyl, C₄-C₁₄        cycloalkylcarbonyl, C₂-C₁₂ alkoxycarbonyl, C₄-C₁₆        cycloalkoxycarbonyl, C₅-C₁₄ cycloalkylalkoxycarbonyl, C₂-C₁₂        alkylaminocarbonyl, C₃-C₁₄ dialkylaminocarbonyl, C₄-C₁₄        cycloalkylaminocarbonyl, C₂-C₉ cyanoalkyl, C₁-C₁₀ hydroxyalkyl,        C₄-C₁₄ cycloalkenylalkyl, C₂-C₁₂ haloalkoxyalkyl, C₂-C₁₂        alkoxyhaloalkyl, C₂-C₁₂ haloalkoxyhaloalkyl, C₄-C₁₄        halocycloalkoxyalkyl, C₄-C₁₄ cycloalkenyloxyalkyl, C₄-C₁₄        halocycloalkenyloxyalkyl, C₃-C₁₄ dialkoxyalkyl, C₃-C₁₄        alkoxyalkylcarbonyl, C₃-C₁₄ alkoxycarbonylalkyl or C₂-C₁₂        haloalkoxycarbonyl;    -   W¹ is C₁-C₆ alkylene;    -   W² is —CH₂—;    -   R² is phenyl or —W³(phenyl), each optionally substituted on ring        members with up to five substituents selected from R²¹; or -G;        C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,        C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈        halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl,        C₄-C₁₀ cycloalkoxyalkyl, C₄-C₁₀ cycloalkoxylalkoxyalkyl, C₃-C₁₀        alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈        alkylcarbonyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl,        C₂-C₈ alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀        halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀        halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₁-C₆ alkoxy,        C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy,        C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy,        C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈ alkoxyalkoxy,        C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀        cycloalkylcarbonyloxy, C₃-C₁₀ alkylcarbonylalkoxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆        alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl,        C₁-C₆ haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₃-C₈        trialkylsilyl, C₃-C₈ cycloalkenyloxy, C₃-C₈ halocycloalkenyloxy,        C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyhaloalkoxy, C₂-C₈        haloalkoxyhaloalkoxy, C₃-C₁₀ alkoxycarbonylalkoxy, C₂-C₈        alkyl(thiocarbonyl)oxy, C₃-C₈ cycloalkylsulfinyl or C₃-C₁₀        halotrialkylsilyl;    -   W³ is —CH₂—;    -   W⁴ is —CH₂—;    -   R¹ and R² are taken together along with the atoms to which they        are attached to make a 6- or 7-membered unsaturated, partially        unsaturated or fully unsaturated ring along with members        consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur        atoms or up to two —S(O)—, —S(O)₂—, —C(O)— groups optionally        substituted on carbon atom ring members selected from halogen,        cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆        haloalkyl, C₃-C₈ cycloalkyl and C₂-C₈ alkoxyalkyl; and phenyl        optionally substituted with up to 5 substituents selected from        cyano, nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆        haloalkoxy; and optionally substituted on nitrogen ring members        selected from H and C₁-C₆ alkyl; and phenyl optionally        substituted with up to 5 substituents selected from cyano,        nitro, halogen, C₁-C₆ alkyl, C₁-C₆ alkoxy and C₁-C₆ haloalkoxy;    -   R³ is hydroxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈        haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy or C₃-C₁₀        alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy,        phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each        optionally substituted on ring members with up to two        substituents selected from R²¹;    -   M⁺ is a sodium or potassium metal cation;    -   R⁹ is C₁-C₆ alkyl;    -   R¹⁰ is H, halogen or C₁-C₆ alkyl;    -   R¹¹ is H or C₁-C₆ alkyl;    -   R¹² is H, halogen, cyano, hydroxy, amino or C₁-C₆ alkyl;    -   R¹³ is cyano or nitro;    -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H or CH₃;    -   R¹⁴ and R¹⁸ are taken together as —CH₂CH₂CH₂— or —CH═CHCH₂—;    -   R²⁰ is H or CH₃;    -   T is —CH₂CH₂— or —CH═CH—;    -   each G is G-1 through G-20 (as depicted in Embodiment 79);    -   r is 0, 1, 2 or 3;    -   each R²¹ is independently halogen, cyano, hydroxy, nitro, —CHO,        —SH, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,        C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,        C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl        or C₃-C₈ cycloalkylsulfonyl; and each R²² is independently C₁-C₆        alkyl or C₁-C₆ haloalkyl.

Embodiment B

A compound of Embodiment A wherein

-   -   X is CH;    -   A is A-3 or A-5;    -   B² is C-3;    -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),        —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally        substituted on ring members with up to five substituents        selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈        cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl or C₂-C₈        alkylsulfonylalkyl;    -   R² is phenyl or —W³(phenyl), each optionally substituted on ring        members with up to two substituents selected from R²¹; or C₁-C₆        alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆        alkylthio or C₁-C₆ alkylsulfonyl;    -   R³ is hydroxy or —O⁻M⁺; or phenylsulfonyloxy optionally        substituted on ring members with up to two substituents selected        from R²¹;    -   R⁹ is CH₂CH₃;    -   R¹⁰ is H or CH₃;    -   W¹ is —CH₂—;    -   W³ is —CH₂—;    -   G is G-13, G-14, G-15, G-16 or G-17; and    -   each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment C

A compound of Embodiment A wherein

-   -   A is A-1, A-3 or A-5;    -   B¹ is C-1;    -   B² is C-3;    -   B³ is C-1;    -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),        —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally        substituted on ring members with up to five substituents        selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈        cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀        alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₁₂ alkylsulfonylalkyl or C₂-C₈        alkylsulfonylalkyl;    -   W¹ is —CH₂—;    -   R² is phenyl or —W³(phenyl), each optionally substituted on ring        members with up to two substituents selected from R²¹; or -G or;        or C₁-C₆ alkyl or C₃-C₈ cycloalkyl;    -   R¹ and R² are taken together along with the atoms to which they        are attached to make an unsubstituted 7-membered partially        unsaturated ring;    -   R³ is hydroxy or C₂-C₈ alkylcarbonyloxy;    -   R⁹ is CH₂CH₃;    -   R¹⁰ is H or CH₃;    -   G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20; and    -   R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment D

A compound of Embodiment C wherein

-   -   A is A-1 or A-3;    -   R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,        2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl,        4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl,        3,5-dimethylphenyl, 3,4-dimethoxyphenyl, 2,3-dimethylphenyl,        3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or        5-chloro-2-methylphenyl;    -   R² is phenyl, 2-methylphenyl, 3-methylphenyl, 3-bromophenyl,        3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or        3,5-difluorophenyl;    -   R³ is hydroxy or —OC(═O)CH₂CH(CH₃)₂;    -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H or CH₃; and T is —CH₂CH₂—.

Embodiment E

A compound of Embodiment D wherein

-   -   A is A-1;    -   R¹ is phenyl, 4-ethylphenyl, 4-methoxyphenyl,        3,5-dimethylphenyl, 3,4-dimethoxyphenyl,        3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or        5-chloro-2-methylphenyl;    -   R² is phenyl, 3-chlorophenyl, or 2-methylphenyl;    -   R³ is hydroxy or —OC(═O)CH₂CH(CH₃)₂; and each R¹⁴, R¹⁵, R¹⁸ and        R¹⁹ is H.

Embodiment F

A compound of Embodiment C wherein

-   -   A is A-3;    -   R¹ is n-Pr or —CH₂CH₂OCH₃;    -   R² is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl,        3-fluorophenyl or 3,5-difluorophenyl;    -   R³ is hydroxy; and    -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.

Embodiment G

A compound of Embodiment C wherein

-   -   A is A-1;    -   R¹ is -G or —W²G; C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈        alkoxyalkyl;    -   G is G-19 or G-20;    -   R² is phenyl, 2-methylphenyl, 3-methylphenyl, 4-chlorophenyl,        3-fluorophenyl or 3,5-difluorophenyl;    -   R³ is hydroxy; and    -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.

Embodiment H

A compound of Embodiment C wherein

-   -   A is A-1;    -   R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or —CH₂CH₂CH₂OCH₃;    -   R² is 3-thienyl or 2-thienyl;    -   R³ is hydroxy; and    -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.

Specific embodiments include a compound of Formula 1 selected from:

-   5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone    (Compound 2),-   5-[(2-hydroxy-6-oxo-1-cyclohexane-1-yl)carbonyl]-3-(3-methoxypropyl)-2-(3-methylphenyl)-4(3H)-pyrimidinone    (Compound 118),-   5-[(2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone    (Compound 97),-   5-[(2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(4-methoxyphenyl)-2-phenyl-4(3H)-pyrimidinone    (Compound 4),-   5-[(2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-3-(3-methoxypropyl)-2-phenyl-4(3H)-pyrimidinone    (Compound 81) and-   3-cyclohexyl-5-[(2-hydroxy-6-oxo-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone    (Compound 128).

Embodiments of the present invention as described in the Summary of theInvention also include (where Formula 1Q from the Summary of theInvention as used in the following Embodiments includes N-oxides andsalts thereof):

Embodiment 1Q

A compound of Formula 1Q wherein A′ is A′-1, A′-3 or A′-5.

Embodiment 2Q

A compound of Embodiment 2Q wherein A′ is A′-1 or A′-3.

Embodiment 3Q

A compound of Embodiment 3Q wherein A′ is A′-1.

Embodiment 4Q

A compound of Embodiment 4Q wherein A′ is A′-3.

Embodiment 5Q

A compound of Formula 1Q or any one of Embodiments 1Q through 4Q whereinB¹ is C-1.

Embodiment 6Q

A compound of Formula 1Q or any one of Embodiments 1Q through 4Q whereinB¹ is C-2.

Embodiment 7Q

A compound of Formula 1Q or any one of Embodiments 1Q through 6Q whereinB² is C-3.

Embodiment 8Q

A compound of Formula 1Q or any one of Embodiments 1Q through 9Q whereinB² is C-4.

Embodiment 9Q

A compound of Formula 1Q or any one of Embodiments 1Q through 8Q whereinB³ is C-1.

Embodiment 10Q

A compound of Formula 1Q or any one of Embodiments 1Q through 8Q whereinB³ is C-2.

Embodiment 11Q

A compound of Formula 1Q or any one of Embodiments 1Q through 10Qwherein R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),—W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted onring members with up to five substituents selected from R²¹; or -G or—W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₁₂alkylsulfinylalkyl or C₂-C₈ alkylsulfonylalkyl.

Embodiment 12Q

A compound of Embodiment 11Q wherein R¹ is phenyl or —W¹(phenyl), eachoptionally substituted on ring members with up to two substituentsselected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀alkylcycloalkyl or C₄-C₁₀ alkoxycycloalkyl.

Embodiment 13Q

A compound of Embodiment 12Q wherein R¹ is phenyl, 2-fluorophenyl,3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl,3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl,3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl,4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 14Q

A compound of Embodiment 13Q wherein R¹ is phenyl, 4-ethylphenyl,4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl,3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or5-chloro-2-methylphenyl. Embodiment 15Q. A compound of Embodiment 14Qwherein R¹ is phenyl, 3,4-dimethoxyphenyl or 5-chloro-2-methylphenyl.

Embodiment 16Q

A compound of Embodiment 15Q wherein R¹ is phenyl.

Embodiment 17Q

A compound of Embodiment 14Q wherein R¹ is 3,4-dimethoxyphenyl.

Embodiment 18Q

A compound of Embodiment 14Q wherein R¹ is 5-chloro-2-methylphenyl.

Embodiment 19Q

A compound of Formula 1Q or any one of Embodiments 1 through 16Q whereinR¹ is other than phenyl.

Embodiment 20Q

A compound of Embodiment 11Q wherein R¹ is -G or —W²G; C₁-C₆ alkyl,C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 21Q

A compound of Embodiment 20Q wherein R¹ is -G or —W²G.

Embodiment 22Q

A compound of Embodiment 20Q wherein R¹ is C₁-C₆ alkyl, C₃-C₈ cycloalkylor C₂-C₈ alkoxyalkyl.

Embodiment 23Q

A compound of Embodiment 22Q wherein R¹ is n-Pr, i-Pr, n-Bu, c-hexyl,—CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or —CH₂CH₂OCH₂CH₃.

Embodiment 24Q

A compound of Embodiment 23Q wherein R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or—CH₂CH₂CH₂OCH₃.

Embodiment 25Q

A compound of Formula 1Q or any one of Embodiments 1Q through 12Qwherein W¹ is C₁-C₆ alkylene.

Embodiment 26Q

A compound of Embodiment 25Q wherein W¹ is —CH₂—.

Embodiment 27Q

A compound of Formula 1Q or any one of Embodiments 1Q through 12Q, 20Qor 21Q wherein W² is —CH₂—.

Embodiment 28Q

A compound of Formula 1Q or any one of Embodiments Embodiment 1Q through27Q wherein R² is phenyl or —W³(phenyl), each optionally substituted onring members with up to two substituents selected from R²¹; or -G or; orC₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 29Q

A compound of Embodiment 28Q wherein R² is phenyl optionally substitutedon ring members with up to two substituents selected from R²¹; or -G; orC₁-C₆ alkyl, C₃-C₈ cycloalkyl.

Embodiment 30Q

A compound of Embodiment 29Q wherein R² is phenyl, 2-methylphenyl,3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl,3-fluorophenyl or 3,5-difluorophenyl.

Embodiment 31Q

A compound of Embodiment 30Q wherein R² is phenyl.

Embodiment 32Q

A compound of Formula 1Q or any one of Embodiments 1Q through 30Qwherein R² is other than phenyl.

Embodiment 33Q

A compound of Embodiment 32Q wherein R² is 3-thienyl or 2-thienyl.

Embodiment 34Q

A compound of Embodiment 33Q wherein R² is n-propyl, n-butyl, orcyclopropyl.

Embodiment 35Q

A compound of Formula 1Q or any one of Embodiments 1Q through 28Qwherein W³ is —CH₂—.

Embodiment 36Q

A compound of Formula 1Q or any one of Embodiments 1Q through 3Q, 7Q and14Q through 51Q wherein R⁹ is C₁-C₆ alkyl.

Embodiment 37Q

A compound of Formula 1Q or any one of Embodiments 1Q or 11Q through 36Qwherein R⁹ is CH₂CH₃.

Embodiment 38Q

A compound of Formula 1Q or any one of Embodiments 1Q or 11Q through 36Qwherein R¹⁰ is H, halogen or C₁-C₆ alkyl.

Embodiment 39Q

A compound of Embodiment 38Q wherein R¹⁰ is H or CH₃.

Embodiment 40Q

A compound of Formula 1Q or any one of Embodiments 1Q through 39Qwherein when instances of R¹⁴ and R¹⁸ are taken alone (i.e. R¹⁴ and R¹⁸are not taken together as alkylene or alkenylene), then independentlysaid instances of R¹⁴ and R¹⁸ are H or C₁-C₆ alkyl.

Embodiment 41Q

A compound of Embodiment 40Q wherein when instances of R¹⁴ and R¹⁸ aretaken alone, then independently said instances of R¹⁴ and R¹⁸ are H orCH₃.

Embodiment 42Q

A compound of Embodiment 41Q wherein when instances of R¹⁴ and R¹⁸ aretaken alone, then independently said instances of R¹⁴ and R¹⁸ are H.

Embodiment 43Q

A compound of Formula 1Q or any one of Embodiments 1Q through 42Qwherein independently each R¹⁵ and R¹⁹ is is H or CH₃.

Embodiment 44Q

A compound of Embodiment 43Q wherein independently each R¹⁵ and R¹⁹ isH.

Embodiment 45Q

A compound of Formula 1Q or any one of Embodiments 1Q through 44Qwherein R²⁰ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl or C₃-C₈ cycloalkyl.

Embodiment 46Q

A compound of Embodiment 45Q wherein R²⁰ is H or CH₃.

Embodiment 47Q

A compound of Formula 1Q or any one of Embodiments 1Q, 2Q, 4Q, 7Q, 8Qand 11Q through 46Q wherein T is —CH₂CH₂— or —CH═CH—.

Embodiment 48Q

A compound of Embodiment 47Q wherein T is —CH₂CH₂—.

Embodiment 49Q

A compound of Formula 1Q or any one of Embodiments 1Q through 48Qwherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted inEmbodiment 79).

Embodiment 50Q

A compound of Embodiment 49Q wherein when R¹ is G, then G is G-19 orG-20.

Embodiment 51Q

A compound of Embodiment 50Q wherein when R¹ is G, then G is G-19.

Embodiment 52Q

A compound of Embodiment 50Q wherein when R¹ is G, then G is G-20.

Embodiment 53Q

A compound of Embodiment 49Q wherein when R² is G, then G is G-2, G-3 orG-15.

Embodiment 54Q

A compound of Embodiment 53Q wherein when R² is G, then G is G-2.

Embodiment 55Q

A compound of Embodiment 53Q wherein when R² is G, then G is G-3.

Embodiment 56Q

A compound of Formula 1Q or any one of Embodiments 1Q through 55Qwherein each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment 57Q

A compound of Embodiment 56Q wherein each R²¹ is independently fluorine,chlorine, bromine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment 58Q

A compound of Formula 1Q or any one of Embodiments 1Q through 57Qwherein each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 59Q

A compound of Embodiment 58Q wherein each R²² is independently CH₃ orCH₂CF₃.

Embodiments of the present invention as described in the Summary of theInvention also include (where Formula 1R from the Summary of theInvention as used in the following Embodiments include N-oxides andsalts thereof):

Embodiment 1R

A compound of Formula 1R wherein R¹ is phenyl, —W¹(phenyl),—W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl),each optionally substituted on ring members with up to five substituentsselected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl,C₂-C₈ alkylthioalkyl, C₂-C₁₂ alkylsulfinylalkyl or C₂-C₈alkylsulfonylalkyl.

Embodiment 2R

A compound of Embodiment 1R wherein R¹ is phenyl or —W¹(phenyl), eachoptionally substituted on ring members with up to two substituentsselected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀alkylcycloalkyl or C₄-C₁₀ alkoxycycloalkyl.

Embodiment 3R

A compound of Embodiment 2R wherein R¹ is phenyl, 2-fluorophenyl,3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl,3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl,3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl,4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 4R

A compound of Embodiment 3R wherein R¹ is phenyl, 4-ethylphenyl,4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl,3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or5-chloro-2-methylphenyl.

Embodiment 5R

A compound of Embodiment 4R wherein R¹ is phenyl, 3,4-dimethoxyphenyl or5-chloro-2-methylphenyl.

Embodiment 6R

A compound of Embodiment 5R wherein R¹ is phenyl.

Embodiment 7R

A compound of Embodiment 4R wherein R¹ is 3,4-dimethoxyphenyl.

Embodiment 8R

A compound of Embodiment 4R wherein R¹ is 5-chloro-2-methylphenyl.

Embodiment 9R

A compound of Formula 1R or any one of Embodiments 1R through 8R whereinR¹ is other than phenyl.

Embodiment 10R

A compound of Formula 1R or any one of Embodiments 1R and 2R R whereinR¹ is -G or —W²G; C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 11R

A compound of Embodiment 10R wherein R¹ is -G or —W²G.

Embodiment 12R

A compound of Embodiment 10R wherein R¹ is C₁-C₆ alkyl, C₃-C₈cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 13R

A compound of Embodiment 12R wherein R¹ is n-Pr, i-Pr, n-Bu, c-hexyl,—CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or —CH₂CH₂OCH₂CH₃.

Embodiment 14R

A compound of Embodiment 13R wherein R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or—CH₂CH₂CH₂OCH₃.

Embodiment 15R

A compound of Formula 1R or any one of Embodiments 1R and 2R wherein W¹is C₁-C₆ alkylene.

Embodiment 16R

A compound of Embodiment 15R wherein W¹ is —CH₂—.

Embodiment 17R

A compound of Formula 1R or any one of Embodiments 1R, 2R 10R and 11Rwherein W² is —CH₂—.

Embodiment 18R

A compound of Formula 1R or any one of Embodiments Embodiment 1R through17R wherein R² is phenyl or —W³(phenyl), each optionally substituted onring members with up to two substituents selected from R²¹; or -G or; orC₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 19R

A compound of Embodiment 18R wherein R² is phenyl optionally substitutedon ring members with up to two substituents selected from R²¹; or -G; orC₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 20R

A compound of Embodiment 19R wherein R² is phenyl, 2-methylphenyl,3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl,3-fluorophenyl or 3,5-difluorophenyl.

Embodiment 21R

A compound of Embodiment 20R wherein R² is phenyl.

Embodiment 22R

A compound of Formula 1R or any one of Embodiments 1R through 21Rwherein R² is other than phenyl.

Embodiment 23R

A compound of Embodiment 22R wherein R² is 3-thienyl or 2-thienyl.

Embodiment 24R

A compound of Embodiment 23R wherein R² is n-propyl, n-butyl, orcyclopropyl.

Embodiment 25R

A compound of Formula 1R or any one of Embodiments 1R through 18Rwherein W³ is —CH₂—.

Embodiment 26R

A compound of Formula 1R or any one of Embodiments 1R through 25Rwherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted inEmbodiment 79).

Embodiment 27R

A compound of Embodiment 26R wherein when R¹ is G, then G is G-19 orG-20.

Embodiment 28R

A compound of Embodiment 27R wherein when R¹ is G, then G is G-19.

Embodiment 29R

A compound of Embodiment 28R wherein when R¹ is G, then G is G-20.

Embodiment 30R

A compound of Embodiment 26R wherein when R² is G, then G is G-2, G-3 orG-15.

Embodiment 31R

A compound of Embodiment 30R wherein when R² is G, then G is G-2.

Embodiment 32R

A compound of Embodiment 31R wherein when R² is G, then G is G-3.

Embodiment 33R

A compound of Formula 1R or any one of Embodiments 1R through 32Rwherein each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment 34R

A compound of Embodiment 33R wherein each R²¹ is independently fluorine,chlorine, bromine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment 35R

A compound of Formula 1R or any one of Embodiments 1R through 32Rwherein each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 36R

A compound of Embodiment 35R wherein each R²² is independently CH₃ orCH₂CF₃.

Embodiments of the present invention as described in the Summary of theInvention also include (where Formula 1S from the Summary of theInvention as used in the following Embodiments includes N-oxides andsalts thereof):

Embodiment 1S

A compound of Formula 1S wherein R¹ is phenyl, —W¹(phenyl),—W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl),each optionally substituted on ring members with up to five substituentsselected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl,C₂-C₈ alkylthioalkyl, C₂-C₁₂ alkylsulfinylalkyl or C₂-C₈alkylsulfonylalkyl.

Embodiment 2S

A compound of Embodiment 1S wherein R¹ is phenyl or —W¹(phenyl), eachoptionally substituted on ring members with up to two substituentsselected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ alkoxycycloalkyl.

Embodiment 3S

A compound of Embodiment 2S wherein R¹ is phenyl, 2-fluorophenyl,3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl, 2-methylphenyl,3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl,3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl,4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl.

Embodiment 4S

A compound of Embodiment 3S wherein R¹ is phenyl, 4-ethylphenyl,4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl,3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or5-chloro-2-methylphenyl.

Embodiment 5S

A compound of Embodiment 4S wherein R¹ is phenyl, 3,4-dimethoxyphenyl or5-chloro-2-methylphenyl.

Embodiment 6S

A compound of Embodiment 5S wherein R¹ is phenyl.

Embodiment 7S

A compound of Embodiment 4S wherein R¹ is 3,4-dimethoxyphenyl.

Embodiment 8S

A compound of Embodiment 4S wherein R¹ is 5-chloro-2-methylphenyl.

Embodiment 9S

A compound of Formula 1S or any one of Embodiments 1S through 8S whereinR¹ is other than phenyl.

Embodiment 10S

A compound of Formula 1S or any one of Embodiments 1S and 2S wherein R¹is -G or —W²G; C₁-C₆ alkyl, C₃-C₈ cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 11S

A compound of Embodiment 10S wherein R¹ is -G or —W²G.

Embodiment 12S

A compound of Embodiment 10S wherein R¹ is C₁-C₆ alkyl, C₃-C₈cycloalkyl, or C₂-C₈ alkoxyalkyl.

Embodiment 13S

A compound of Embodiment 12S wherein R¹ is n-Pr, i-Pr, n-Bu, c-hexyl,—CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or —CH₂CH₂OCH₂CH₃.

Embodiment 14S

A compound of Embodiment 13S wherein R¹ is n-Pr, c-hexyl, —CH₂CH₂OCH₃ or—CH₂CH₂CH₂OCH₃.

Embodiment 15S

A compound of Formula 1S or any one of Embodiments 1S and 2S wherein W¹is C₁-C₆ alkylene.

Embodiment 16S

A compound of Embodiment 15S wherein W¹ is —CH₂—.

Embodiment 17S

A compound of Formula 1Sor any one of Embodiments 1S, 2S 10S and 11Swherein W² is —CH₂—.

Embodiment 18S

A compound of Formula 1S or any one of Embodiments Embodiment 1S through17S wherein R² is phenyl or —W³(phenyl), each optionally substituted onring members with up to two substituents selected from R²¹; or -G or; orC₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment 19S

A compound of Embodiment 18S wherein R² is phenyl optionally substitutedon ring members with up to two substituents selected from R²¹; or -G; orC₁-C₆ alkyl, C₃-C₈ cycloalkyl.

Embodiment 20S

A compound of Embodiment 19S wherein R² is phenyl, 2-methylphenyl,3-methylphenyl, 3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl,3-fluorophenyl or 3,5-difluorophenyl.

Embodiment 21S

A compound of Embodiment 20S wherein R² is phenyl.

Embodiment 22S

A compound of Formula 1S or any one of Embodiments 1S through 21Swherein R² is other than phenyl.

Embodiment 23S

A compound of Embodiment 22S wherein R² is 3-thienyl or 2-thienyl.

Embodiment 24S

A compound of Embodiment 23S wherein R² is n-propyl, n-butyl, orcyclopropyl.

Embodiment 25S

A compound of Formula 1S or any one of Embodiments 1S through 18Swherein W³ is —CH₂—.

Embodiment 26S

A compound of Formula 1S or any one of Embodiments 1S through 25Swherein G is G-2, G-3, G-9, G-15, G-18, G-19 or G-20 (as depicted inEmbodiment 79).

Embodiment 27S

A compound of Embodiment 26S wherein when R¹ is G, then G is G-19 orG-20.

Embodiment 28S

A compound of Embodiment 27S wherein when R¹ is G, then G is G-19.

Embodiment 29S

A compound of Embodiment 28S wherein when R¹ is G, then G is G-20.

Embodiment 30S

A compound of Embodiment 26S wherein when R² is G, then G is G-2, G-3 orG-15.

Embodiment 31S

A compound of Embodiment 30R wherein when R² is G, then G is G-2.

Embodiment 32S

A compound of Embodiment 31R wherein when R² is G, then G is G-3.

Embodiment 33S

A compound of Formula 1R or any one of Embodiments 1R through 32Rwherein each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment 34S

A compound of Embodiment 33R wherein each R²¹ is independently fluorine,chlorine, bromine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment 35S

A compound of Formula 1R or any one of Embodiments 1R through 32Rwherein each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 36S

A compound of Embodiment 58Q wherein each R²² is independently CH₃ orCH₂CF₃.

Embodiment 37S

A compound of Formula 1S or any on of Embodiments 1S through 36S whereinwhen R²³ is an optionally substituted carbon moiety, R²³ is C₁-C₁₆alkyl; or phenyl or benzyl optionally substituted with halogen, nitro,cyano or hydroxy on ring members.

Embodiment 38S

A compound of Embodiment 37S wherein when R²³ is an optionallysubstituted carbon moiety, R²³ is C₁-C₁₀ alkyl; or phenyl or benzyloptionally substituted with halogen or nitro on ring members.

Embodiment 39S

A compound of Embodiment 38S wherein when R²³ is an optionallysubstituted carbon moiety, R²³ is C₁-C₆ alkyl; or benzyl optionallysubstituted with halogen or nitro on ring members.

Embodiment 40S

A compound of Embodiment 39S wherein when R²³ is an optionallysubstituted carbon moiety, R²³ is C₁-C₆ alkyl; or unsubstituted benzyl.

Embodiment 41S

A compound of Embodiment 40S wherein when R²³ is an optionallysubstituted carbon moiety, R²³ is C₁-C₆ alkyl.

Embodiment 42S

A compound of Embodiment 41S wherein when R²³ is an optionallysubstituted carbon moiety, R²³ is unsubstituted benzyl.

Embodiment 43S

A compound of Embodiment 42S wherein when R²³ is an optionallysubstituted carbon moiety, R²³ is ethyl, n-propyl, n-butyl or i-propyl.

Embodiment 44S

A compound of Embodiment 43S wherein when R²³ is an optionallysubstituted carbon moiety, R²³ is ethyl, n-propyl or i-propyl.

Embodiment 45S

A compound of Embodiment 44S wherein when R²³ is an optionallysubstituted carbon moiety, R²³ is ethyl.

Embodiments of the present invention as described in the Summary of theInvention also include (where Formula 1P as used in the followingEmbodiments includes N-oxides and salts thereof):

Embodiment P1

A compound of Formula 1P wherein X is N.

Embodiment P2

A compound of Formula 1P wherein X is CH.

Embodiment P3

A compound of Formula 1P or any one of Embodiments P1 through P2 whereinY is C(O).

Embodiment P4

A compound of Formula 1P or Embodiment P2 wherein Y is S(O)₂.

Embodiment P5

A compound of Formula 1P or any one of Embodiments P1 through P4 whereinA is A-1, A-3, A-4, A-5 or A-6.

Embodiment P6

A compound of Embodiment P5 wherein A is A-1, A-3, A-5 or A-6.

Embodiment P7

A compound of Embodiment P6 wherein A is A-3 or A-5.

Embodiment P8

A compound of Embodiment P7 wherein A is A-3.

Embodiment P9

A compound of Embodiment P6 wherein A is A-1 or A-6.

Embodiment P10

A compound of Embodiment P9 wherein A is A-1.

Embodiment P11

A compound of Formula 1P or any one of Embodiments P1 through P9 whereinA is other than A-1.

Embodiment P12

A compound of Formula 1P or any one of Embodiments P1 through P11wherein B¹ is C-1.

Embodiment P13

A compound of Formula 1P or any one of Embodiments P1 through P11wherein B¹ is C-2.

Embodiment P14

A compound of Formula 1P or any one of Embodiments P1 through P13wherein B² is C-3.

Embodiment P15

A compound of Formula 1P or any one of Embodiments P1 through P13wherein B² is C-4.

Embodiment P16

A compound of Formula 1P or any one of Embodiments P1 through P13wherein B² is C-6

Embodiment P17

A compound of Formula 1P or any one of Embodiments P1 through P13wherein B² is C-7.

Embodiment P18

A compound of Formula 1P or any one of Embodiments P1 through P17wherein B³ is C-1.

Embodiment P19

A compound of Formula 1P or any one of Embodiments P1 through P17wherein B³ is C-2.

Embodiment P20

A compound of Formula 1P or any one of Embodiments P1 through P19wherein R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),—W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionallysubstituted on ring members with up to five substituents selected fromR²¹; or -G or —W²G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN,—C(═O)NHOH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₆ alkyl, C₂-C₆alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl,C₃-C₁₀ dialkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀cycloalkylaminoalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl,C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₄-C₁₀cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀dialkoxyalkyl, C₃-C₁₀ alkoxyalkylcarbonyl, C₃-C₁₀ alkoxycarbonylalkyl orC₂-C₈ haloalkoxycarbonyl.

Embodiment P21

A compound of Embodiment P20 wherein R¹ is phenyl, —W¹(phenyl),—W¹(S-phenyl), —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl),each optionally substituted on ring members with up to five substituentsselected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈alkylthioalkyl or C₂-C₈ alkylsulfonylalkyl.

Embodiment P22

A compound of Embodiment P21 wherein R¹ is phenyl or —W¹(phenyl), eachoptionally substituted on ring members with up to two substituentsselected from R²¹; or C₁-C₆ alkyl or C₂-C₆ alkenyl.

Embodiment P23

A compound of Embodiment P22 wherein R¹ is phenyl, 2-fluorophenyl,3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl,4-chlorophenyl, 4-methylphenyl, 2-methylphenyl, 4-methoxyphenyl,2,3-dimethylphenyl, CH₂(phenyl), CH₃ or CH₂CH₃.

Embodiment P24

A compound of Embodiment P23 wherein R¹ is phenyl.

Embodiment P25

A compound of Formula 1P or any one of Embodiments P1 through P22wherein W¹ is C₁-C₆ alkylene.

Embodiment P26

A compound of Embodiment P25 wherein W¹ is —CH₂—.

Embodiment P27

A compound of Formula 1P or any one of Embodiments P1 through P21 or P25or P26 wherein W² is —CH₂—.

Embodiment P28

A compound of Formula 1P or any one of Embodiments P1 through P27wherein R² is phenyl or —W³(phenyl), each optionally substituted on ringmembers with up to five substituents selected from R²¹; or C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl,C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀cycloalkoxyalkyl, C₄-C₁₀ cycloalkoxylalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl,C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀cycloalkylcarbonyloxy, C₃-C₁₀ alkylcarbonylalkoxy, C₁-C₆ alkylthio,C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈cycloalkylsulfonyl, C₃-C₈ trialkylsilyl, C₃-C₈ cycloalkenyloxy, C₃-C₈halocycloalkenyloxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyhaloalkoxy,C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₁₀ alkoxycarbonylalkoxy, C₂-C₈alkyl(thiocarbonyl)oxy, C₃-C₈ cycloalkylsulfinyl or C₃-C₁₀halotrialkylsilyl.

Embodiment P29

A compound of Embodiment P28 wherein R² is phenyl or —W³(phenyl), eachoptionally substituted on ring members with up to two substituentsselected from R²¹; or C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl,C₁-C₆ alkoxy, C₁-C₆ alkylthio or C₁-C₆ alkylsulfonyl.

Embodiment P30

A compound of Embodiment P29 wherein R² is phenyl or CH₂(phenyl), eachoptionally substituted on ring members with up to two substituentsselected from R²¹; or C₁-C₆ alkyl, C₃-C₈ cycloalkyl or C₁-C₆ alkylthio.

Embodiment P31

A compound of Embodiment P30 wherein R² is phenyl, 2-chlorophenyl,3-chlorophenyl, 4-chlorophenyl, CH₂CH₃, cyclopropyl or SCH₃.

Embodiment P32

A compound of Formula 1P or any one of Embodiments P1 through P29wherein W³ is C₁-C₆ alkylene.

Embodiment P33

A compound of Embodiment P32 wherein W³ is —CH₂—.

Embodiment P34

A compound of Formula 1P or any one of Embodiments P1 through P27 or P32or P33 wherein W⁴ is —CH₂—.

Embodiment P35

A compound of Formula 1P or any one of Embodiments P1 through P34wherein R³ is hydroxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy or C₃-C₁₀alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy,phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, eachoptionally substituted on ring members with up to two substituentsselected from R²¹.

Embodiment P36

A compound of Embodiment P35 wherein R³ is hydroxy or —O⁻M⁺; orphenylsulfonyloxy optionally substituted with up to two substituentsselected from R²¹.

Embodiment P37

A compound of Embodiment P36 wherein R³ is hydroxy; or phenylsulfonyloxysubstituted with CH₃ at the 4-position.

Embodiment P38

A compound of Formula 1P or any one of Embodiments P1 through P36wherein M⁺ is a sodium or potassium metal cation.

Embodiment P39

A compound of Formula 1P or any of Embodiments P1 through P7 and P12through P38 wherein R⁴, R⁵, R⁶ and R⁷ are each independently H, or C₁-C₆alkyl.

Embodiment P40

A compound of Formula 1P or any one of Embodiments P1 through P7 and 12through 39 wherein R⁸ is C₁-C₆ alkyl or C₃-C₈ cycloalkyl.

Embodiment P41

A compound of Embodiment P40 wherein R⁸ is CH₃, CH₂CH₃ or cyclopropyl.

Embodiment P42

A compound of Formula 1P or any one of Embodiments P1 through P9 and 12through 41 wherein R⁹ is C₁-C₆ alkyl.

Embodiment P43

A compound of Embodiment P42 wherein R⁹ is CH₂CH₃.

Embodiment P44

A compound of Formula 1P or any one of Embodiments P1 through P9 and 12through 41 wherein R¹⁰ is H, halogen or C₁-C₆ alkyl.

Embodiment P45

A compound of Embodiment P44 wherein R¹⁰ is H or CH₃.

Embodiment P46

A compound of Formula 1P or any one of Embodiments P1 through P8, P10,and P12 through P45 wherein R¹¹ is H or C₁-C₆ alkyl.

Embodiment P47

A compound of Embodiment P46 wherein R¹¹ is H.

Embodiment P48

A compound of Formula 1P or any one of Embodiments P1 through P8, P10,and P12 through P47 wherein R¹² is H, halogen, cyano, hydroxy, amino orC₁-C₆ alkyl.

Embodiment P49

A compound of Embodiment P48 wherein R¹² is H, halogen, cyano, C₁-C₆alkyl or C₃-C₈ cycloalkyl.

Embodiment P50

A compound of Embodiment P49 wherein R¹² is CH₃, CH₂CH₃ or cyclopropyl.

Embodiment P51

A compound of Formula 1P or any one of Embodiments P1 through P6 and P12through P50 wherein R¹³ is H, halogen, cyano or nitro.

Embodiment P52

A compound of Embodiment P51 wherein R¹³ is cyano or nitro.

Embodiment P53

A compound of Formula 1P or any one of Embodiments P1 through P52wherein when instances of R¹⁴ and R¹⁸ are taken alone (i.e. R¹⁴ and R¹⁸are not taken together as alkylene or alkenylene), then independentlysaid instances of R¹⁴ and R¹⁸ are H or C₁-C₆ alkyl.

Embodiment P53a

A compound of Embodiment P53 wherein when instances of R¹⁴ and R¹⁸ aretaken alone, then independently said instances of R¹⁴ and R¹⁸ are H orCH₃.

Embodiment P53b

A compound of Embodiment P53a wherein when instances of R¹⁴ and R¹⁸ aretaken alone, then independently said instances of R¹⁴ and R¹⁸ are H.

Embodiment P53c

A compound of Formula 1P or any one of Embodiments P1 through P53bwherein when instances of R¹⁴ and R¹⁸ are taken together, then saidinstances of R¹⁴ and R¹⁸ are taken together as —CH₂CH₂CH₂— or—CH═CH—CH₂—.

Embodiment P53d

A compound of Formula 1P or any one of Embodiments P1 through P53bwherein all instances of R¹⁴ and R¹⁸ are taken alone.

Embodiment P54

A compound of Formula 1P or any one of Embodiments P1 through P53dwherein independently each R¹⁵ and R¹⁹ is H or C₁-C₆ alkyl.

Embodiment P54a

A compound of Embodiment P54 wherein independently each R¹⁵ and R¹⁹ is Hor CH₃.

Embodiment P55

A compound of Embodiment P54a wherein independently each R¹⁵ and R¹⁹ isH.

Embodiment P56

A compound of Formula 1P or any one of Embodiments P1 through P55wherein R²⁰ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl or C₃-C₈ cycloalkyl.

Embodiment P57

A compound of Embodiment P56 wherein R²⁰ is H or CH₃.

Embodiment P58

A compound of Formula 1P or any one of Embodiments P1 through P57wherein T is —CH₂CH₂— or —CH═CH—.

Embodiment P59

A compound of Formula 1P or any one of Embodiments P1 through P58wherein each G is independently a 5- or 6-membered heterocyclic ringoptionally substituted with up to five substituents selected from R²¹ oncarbon ring members and R²² on nitrogen ring members.

Embodiment P60

A compound of Embodiment P59 wherein G is selected from

-   -   r is 0, 1, 2 or 3.

Embodiment P61

A compound of Embodiment P60 wherein G is G-13, G-14, G-15, G-16 orG-17.

Embodiment P62

A compound of Formula 1P or any one of Embodiments P1 through P61wherein each R²¹ is independently halogen, cyano, hydroxy, nitro, —CHO,—SH, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₃-C₈ cycloalkenyl,C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl,C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₅ cyanoalkyl, C₁-C₆hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆haloalkenyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆alkylthio, C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl or C₃-C₈ cycloalkylsulfonyl.

Embodiment P63

A compound of Embodiment P62 wherein each R²¹ is independently halogen,nitro, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy orC₁-C₆ alkylthio.

Embodiment P64

A compound of Embodiment P61 wherein each R²¹ is independently fluorine,chlorine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment P65

A compound of Formula 1P or any one of Embodiments P1 through P64wherein each R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment P66

A compound of Embodiment P1 through 65 wherein each R²² is independentlyCH₃ or CH₂CF₃.

This invention also includes a herbicidal mixture of (a) a compound ofFormula 1P and (b) an active ingredient selected from photosystem IIinhibitors.

Embodiment P67

A herbicidal mixture comprising (a) a compound of Formula 1P and (b) anadditional herbicidal ingredient selected from photosystem IIinhibitors.

Embodiment P68

A herbicidal mixture of Embodiment P67 comprising (a) a compound ofFormula 1P and (b) an additional herbicidal compound selected from thegroup consisting of ametryn, amicarbazone, atrazine, bentazon, bromacil,bromoxynil, chlorotoluron, diuron, hexazinone, isoproturon, metribuzin,pyridate, simazine and terbutryn.

Embodiment P69

A herbicidal mixture of Embodiment P68 comprising (a) a compound ofFormula 1P; and (b) bromoxynil.

Embodiments of this invention, including Embodiments P1-P69 above aswell as any other embodiments described herein, can be combined in anymanner, and the descriptions of variables in the embodiments pertain notonly to the compounds of Formula 1P but also to the starting compoundsand intermediate compounds useful for preparing the compounds of Formula1P. In addition, embodiments of this invention, including Embodiments1-66 above as well as any other embodiments described herein, and anycombination thereof, pertain to the compositions and methods of thepresent invention.

Combinations of Embodiments 1-66 are illustrated by:

Embodiment PA

A compound of Formula 1P wherein

-   -   Y is C(O);    -   A is A-1, A-3, A-5 or A-6;    -   R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),        —W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each        optionally substituted on ring members with up to five        substituents selected from R²¹; or -G or —W²G; or cyano,        hydroxy, amino, —C(═O)OH, —C(═O)NHCN, —C(═O)NHOH, —SO₂NH₂,        —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆        alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl,        C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl,        C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀        halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀        cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₃-C₁₀        dialkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀        cycloalkylaminoalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂        cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₂-C₅        cyanoalkyl, C₁-C₆ hydroxyalkyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl, C₂-C₈        haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀        cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀        dialkoxyalkyl, C₃-C₁₀ alkoxyalkylcarbonyl, C₃-C₁₀        alkoxycarbonylalkyl or C₂-C₈ haloalkoxycarbonyl;    -   W¹ is C₁-C₆ alkylene    -   W² is —CH₂—;    -   R² is phenyl or —W³(phenyl), each optionally substituted on ring        members with up to five substituents selected from R²¹; or C₁-C₆        alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆        haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈        halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl,        C₄-C₁₀ cycloalkoxylalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈        alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₄-C₁₀        cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkoxyhaloalkyl,        C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀ halocycloalkoxyalkyl, C₄-C₁₀        cycloalkenyloxyalkyl, C₄-C₁₀ halocycloalkenyloxyalkyl, C₃-C₁₀        dialkoxyalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈        cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy,        C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆        haloalkynyloxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy,        C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₃-C₁₀        alkylcarbonylalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈        cycloalkylsulfonyl, C₃-C₈ trialkylsilyl, C₃-C₈ cycloalkenyloxy,        C₃-C₈ halocycloalkenyloxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈        alkoxyhaloalkoxy, C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₁₀        alkoxycarbonylalkoxy, C₂-C₈ alkyl(thiocarbonyl)oxy, C₃-C₈        cycloalkylsulfinyl or C₃-C₁₀ halotrialkylsilyl;    -   W³ is C₁-C₆ alkylene;    -   W⁴ is —CH₂—;    -   R³ is hydroxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈        haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy or C₃-C₁₀        alkylcarbonylalkoxy; or benzyloxy, phenyloxy, benzylcarbonyloxy,        phenylcarbonyloxy, phenylsulfonyloxy or benzylsulfonyloxy, each        optionally substituted on ring members with up to two        substituents selected from R²¹;    -   M⁺ is a sodium or potassium metal cation;    -   R⁹ is C₁-C₆ alkyl;    -   R¹⁰ is H, halogen or C₁-C₆ alkyl;    -   R¹¹ is H or C₁-C₆ alkyl;    -   R¹² is H, halogen, cyano, hydroxy, amino or C₁-C₆ alkyl;    -   R¹³ is cyano or nitro;    -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is independently H or CH₃; or    -   a pair of R¹⁴ and R¹⁸ is taken together as —CH₂CH₂CH₂— or        —CH═CH—CH₂—;    -   R²⁰ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl or C₃-C₈ cycloalkyl;    -   T is —CH₂CH₂— or —CH═CH—;    -   each G is selected from G-1 through G-23 (as depicted in        Embodiment 79);    -   r is 0, 1, 2 or 3;    -   each R²¹ is independently halogen, cyano, hydroxy, nitro, —CHO,        —SH, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,        C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈        halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈        alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈ alkoxyhaloalkyl,        C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy, C₁-C₆        haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀        cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈        alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆        haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl        or C₃-C₈ cycloalkylsulfonyl; and    -   R²² is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment PB

A compound of Embodiment PA wherein

-   -   X is CH;    -   A is A-3 or A-5;    -   B² is C-3;    -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),        —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally        substituted on ring members with up to five substituents        selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈        cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl or C₂-C₈        alkylsulfonylalkyl;    -   R² is phenyl or —W³(phenyl), each optionally substituted on ring        members with up to two substituents selected from R²¹; or C₁-C₆        alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆        alkylthio or C₁-C₆ alkylsulfonyl;    -   R³ is hydroxy or —O⁻M⁺; or phenylsulfonyloxy optionally        substituted on ring members with up to two substituents selected        from R²¹;    -   R⁹ is CH₂CH₃;    -   R¹⁰ is H or CH₃;    -   W¹ is —CH₂—;    -   W³ is —CH₂—;    -   G is G-13, G-14, G-15, G-16 or G-17; and    -   each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment PC

A compound of Embodiment PA wherein:

-   -   X is CH;    -   A is A-1 or A-6;    -   B¹ is C-1, B² is C-3 and B³ is C-1;    -   R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),        —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally        substituted on ring members with up to five substituents        selected from R²¹; or -G or —W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl,        C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈        cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl,        C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl,        C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl or C₂-C₈        alkylsulfonylalkyl;    -   R² is phenyl or —W³(phenyl), each optionally substituted on ring        members with up to two substituents selected from R²¹; or C₁-C₆        alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₁-C₆ alkoxy, C₁-C₆        alkylthio or C₁-C₆ alkylsulfonyl;    -   R³ is hydroxy or —O⁻M⁺; or phenylsulfonyloxy optionally        substituted on ring members with up to two substituents selected        from R²¹;    -   R¹¹ is H;    -   each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is independently H or CH₃;    -   R¹² is H, halogen, cyano, C₁-C₆ alkyl or C₃-C₈ cycloalkyl;    -   W¹ is —CH₂—;    -   W³ is —CH₂—;    -   G is G-13, G-14, G-15, G-16 or G-17; and    -   each R²¹ is independently halogen, nitro, C₁-C₆ alkyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆ alkylthio.

Embodiment PD

A compound of Embodiment PC wherein:

-   -   A is A-1;    -   R¹ is phenyl or —W¹(phenyl) each optionally substituted on ring        members with up to two substituents selected from R²¹; or C₁-C₆        alkyl or C₂-C₆ alkenyl; R² is phenyl or CH₂(phenyl), each        optionally substituted on ring members with up to two        substituents selected from R²¹; or C₁-C₆ alkyl, C₃-C₈ cycloalkyl        or C₁-C₆ alkylthio;    -   R³ is hydroxy; or phenylsulfonyloxy substituted with CH₃ at the        4-position; and each R²¹ is independently fluorine, chlorine,        CH₃, CF₃, OCH₃, OCF₃ or SCH₃.

Embodiment PE

A compound of Embodiment PD wherein:

-   -   R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl,        2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl,        2-methylphenyl, 4-methoxyphenyl, 2,3-dimethylphenyl,        CH₂(phenyl), CH₃ or CH₂CH₃;    -   R² is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,        CH₂CH₃, c-Pr or SCH₃.

Specific embodiments include the compound of Formula 1P which is:

-   5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone.

This invention also relates to a method for controlling undesiredvegetation comprising applying to the locus of the vegetation aherbicidally effective amount of a compound of the invention (e.g., as acomposition described herein). Of note as embodiments relating tomethods of use are those involving the compounds of embodimentsdescribed above.

This invention also includes herbicidal mixture comprising (a) acompound of Formula 1P and (b) an additional herbicidal ingredientselected from a photosystem II inhibitor. Also noteworthy as embodimentsare herbicidal compositions of the present invention comprising thecompounds of embodiments described above.

“Photosystem II inhibitors” (b1) are chemical compounds that bind to theD-1 protein at the Q_(B)-binding niche and thus block electron transportfrom Q_(A) to Q_(B) in the chloroplast thylakoid membranes. Theelectrons blocked from passing through photosystem II are transferredthrough a series of reactions to form toxic compounds that disrupt cellmembranes and cause chloroplast swelling, membrane leakage, andultimately cellular destruction. The Q_(B)-binding niche has threedifferent binding sites: binding site A binds the triazines such asatrazine, triazinones such as hexazinone, and uracils such as bromacil,binding site B binds the phenylureas such as diuron, and binding site Cbinds benzothiadiazoles such as bentazon, nitriles such as bromoxyniland phenyl-pyridazines such as pyridate. Examples of photosystem IIinhibitors include, but are not limited to ametryn, atrazine, cyanazine,desmetryne, dimethametryn, prometon, prometryne, propazine, simazine,simetryn, terbumeton, terbuthylazine, terbutryne, trietazine,hexazinone, metamitron, metribuzin, amicarbazone, bromacil, lenacil,terbacil, chloridazon, desmedipham, phenmedipham, chlorobromuron,chlorotoluron, chloroxuron, dimefuron, diuron, ethidimuron, fenuron,fluometuron, isoproturon, isouron, linuron, methabenzthiazuron,metobromuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron,propanil, pentanochlor, bromofenoxim, bromoxynil, ioxynil, bentazon,pyridate and pyridafol.

“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxyacid synthase (AHAS), also known as acetolactate synthase (ALS), andthus kill plants by inhibiting the production of the branched-chainaliphatic amino acids such as valine, leucine and isoleucine, which arerequired for DNA synthesis and cell growth. Examples of AHAS inhibitorsinclude but are not limited to amidosulfuron, azimsulfuron,bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron,cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,flupyrsulfuron-methyl (including sodium salt), foramsulfuron,halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl (includingsodium salt), mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl,nicosulfuron, oxasulfuron, primisulfuron-methyl, propyrisulfuron,prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl,sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl,trifloxysulfuron (including sodium salt), triflusulfuron-methyl,tritosulfuron, imazapic, imazamethabenz-methyl, imazamox, imazapyr,imazaquin, imazethapyr, cloransulam-methyl, diclosulam, florasulam,flumetsulam, metosulam, penoxsulam, bispyribac-sodium, pyribenzoxim,pyriftalid, pyrithiobac-sodium, pyriminobac-methyl, thiencarbazone,flucarbazone-sodium and propoxycarbazone-sodium.

“ACCase inhibitors” (b3) are chemical compounds that inhibit theacetyl-CoA carboxylase enzyme, which is responsible for catalyzing anearly step in lipid and fatty acid synthesis in plants. Lipids areessential components of cell membranes, and without them, new cellscannot be produced. The inhibition of acetyl CoA carboxylase and thesubsequent lack of lipid production leads to losses in cell membraneintegrity, especially in regions of active growth such as meristems.Eventually shoot and rhizome growth ceases, and shoot meristems andrhizome buds begin to die back. Examples of ACCase inhibitors includebut are not limited to clodinafop, cyhalofop, diclofop, fenoxaprop,fluazifop, haloxyfop, propaquizafop, quizalofop, alloxydim, butroxydim,clethodim, cycloxydim, pinoxaden, profoxydim, sethoxydim, tepraloxydimand tralkoxydim, including resolved forms such as fenoxaprop-P,fluazifop-P, haloxyfop-P and quizalofop-P and ester forms such asclodinafop-propargyl, cyhalofop-butyl, diclofop-methyl andfenoxaprop-P-ethyl.

Auxin is a plant hormone that regulates growth in many plant tissues.“Auxin mimics” (b4) are chemical compounds mimicking the plant growthhormone auxin, thus causing uncontrolled and disorganized growth leadingto plant death in susceptible species. Examples of auxin mimics includebut are not limited to aminocyclopyrachlor, aminopyralidbenazolin-ethyl, chloramben, clomeprop, clopyralid, dicamba, 2,4-D,2,4-DB, dichlorprop, fluroxypyr, mecoprop, MCPA, MCPB, 2,3,6-TBA,picloram, triclopyr, quinclorac, quinmerac.

“EPSP (5-enol-pyruvylshikimate-3-phosphate) synthase inhibitors” (b5)are chemical compounds that inhibit the enzyme,5-enol-pyruvylshikimate-3-phosphate synthase, which is involved in thesynthesis of aromatic amino acids such as tyrosine, tryptophan andphenylalanine. EPSP inhibitor herbicides are readily absorbed throughplant foliage and translocated in the phloem to the growing points.Glyphosate is a relatively nonselective postemergence herbicide thatbelongs to this group. Glyphosate includes esters and salts such asammonium, isopropylammonium, potassium, sodium (including sesquisodium)and trimesium (alternatively named sulfosate).

One or more of the following methods and variations as described inSchemes 1-18 can be used to prepare the compounds of Formula 1. Thedefinitions of A, B¹, B², B³, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰,R¹² and R¹³ in the compounds of Formulae 1-34 below are as defined abovein the Summary of the Invention unless otherwise noted. Compounds ofFormulae 1a-1h are various subsets of the compounds of Formula 1, andall substituents for Formulae 1a-1h are as defined above for Formula 1.

Compounds of Formula 1a, 1b or 1c (where R³ is hydroxy) can be preparedvia the two-step process shown in Schemes 1a, 1b and 1c respectively.Intermediate 4a, 4b or 4c can be prepared by reacting dione 2 withintermediate 3 where G is a nucleophilic reaction leaving group (e.g.,G¹ is a halogen, alkoxycarbonyl, haloalkylcarbonyloxy,haloalkoxycarbonyloxy, pyridinyl or imidazoyl group). Reaction ofintermediate 4a, 4b or 4c with the appropriate cyano compound (e.g.,acetone cyanohydrin, potassium cyanide, sodium cyanide) in the presenceof a base such as triethylamine or pyridine leads to a compound ofFormula 1a, 1b or 1c. Alternatively a fluoride anion source such aspotassium fluoride or cesium fluoride and optionally in the presence ofa phase transfer catalyst (e.g. tetrabutyl ammonium bromide, etc.) canbe used in this transformation. A solvent such as dimethylsulfoxide,N,N-dimethylformamide, acetonitrile or dichloromethane at ambienttemperature to the reflux temperature of the solvent can lead to acompound of Formula 1a, 1b or 1c. (Formula 1a is Formula 1 wherein A isA-1; Formula 1b is Formula 1 wherein A is A-2; Formula 1c is Formula 1wherein A is A-3.) Alternatively, compounds of Formula 1a, 1b or 1c canbe prepared by Process 2 (in Schemes 1a, 1b and 1c respectively) byreacting dione 2a, 2b or 2c with intermediate 3 in the presence of acyano compound or a fluoride anion source along with a base. Foradditional reaction conditions for this general coupling methodology,see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. andSchirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and referencescited therein.

Compounds of Formula 1a, 1b or 1c can also be prepared as shown inScheme 2, by reacting dione 2a, 2b or 2c with intermediate 3a in thepresence of a base or Lewis acid. For reaction conditions for thisgeneral coupling methodology, see Edmunds, A. in Modern Crop ProtectionCompounds; Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007;Chapter 4.3 and references cited therein.

As shown in Scheme 3, intermediate 4a, 4b or 4c can also be prepared byallowing dione 2a, 2b or 2c to react with acid 6 in the presence of adehydrating condensation agent such as 2-chloro-1-pyridinium iodide(known as the Mukaiyama coupling agent), dicyclohexyl carbodiimide (DCC)or the like and optionally in the presence of a base. For additionalreaction conditions for this general enol ester coupling methodology,see Edmunds, A. in Modern Crop Protection Compounds; Kramer, W. andSchirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 and referencescited therein.

Intermediate 4a, 4b or 4c can also be made by the palladium-catalyzedcarbonylation reaction of a compound of Formula 7 in the presence ofdione 2a, 2b or 2c (Scheme 4). For reaction conditions for this generalenol ester forming methodology, see Edmunds, A. in Modern CropProtection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley,Weinheim, 2007; Chapter 4.3 and references cited therein.

Compounds of Formula 1a, 1b or 1c (where R³ is bonded through oxygen)are prepared by reacting compounds of Formula 1a, 1b or 1c withintermediate 8 where X is a nucleophilic reaction leaving group, alsoknown as a nucleofuge in the presence of a base as shown in Scheme 5.Alternatively, compounds of Formula 1a, 1b and 1c (where R³ is bondedthrough nitrogen, sulfur or carbon) can be prepared using theappropriate halogenating agent followed by nucleophilic addition. Forreaction conditions for this general functionalization method, seeEdmunds, A. or Almisick A. V. in Modern Crop Protection Compounds;Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.3 orChapter 4.4, and references cited therein.

As shown in Scheme 6, compounds of Formula 1d (i.e. Formula 1 wherein Ais A-4 and R³ is OH) can be prepared by the reaction of intermediate 9with intermediate 3 in the presence of a Lewis base, for examplen-butyllithium or lithium diisopropylamide in an appropriate solventsuch as tetrahydrofuran or diethyl ether. For reaction conditions forthis type of transformation, see JP 2003327580.

Compounds of Formula 1e (i.e. Formula 1 wherein A is A-5 and R³ is OH)can be prepared via a two-step process as shown in Scheme 7.Intermediate 12 can be prepared by reacting pyrazole 11 withintermediate 3 where G¹ is a nucleophilic reaction leaving group (i.e.G¹ is a halogen atom, alkoxycarbonyl, haloalkylcarbonyloxy, benzoyloxy,pyridinyl or imidazoyl group). Reaction of intermediate 12 with theappropriate cyano compound in the presence of a base leads to a compoundof Formula 1e. Alternatively, a compound of Formula 1e can be prepareddirectly by reacting intermediate 11 with intermediate 3 (Process 2,Scheme 7) in the presence of a cyano compound or a fluoride anion sourcewith a base. For reaction conditions for this general couplingmethodology, see Almisick A. V. in Modern Crop Protection Compounds;Kramer, W. and Schirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4,and references cited therein.

Compounds of Formula 1f (i.e. Formula 1 wherein A is A-5) wherein R³ isbonded through oxygen can be prepared by reacting a compound of Formula1e with intermediate 8 (where X is a nucleophilic reaction leavinggroup, also known as a nucleofuge) in the presence of a base as shown inScheme 8. Alternatively compounds of Formula 1f wherein R³ is bondedthrough nitrogen, sulfur or carbon can be prepared using the appropriatehalogenating agent followed by nucleophilic displacement. For reactionconditions for these general functionalization methods, see Almisick A.V. in Modern Crop Protection Compounds; Kramer, W. and Schirmer, U.,Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and references cited therein.

Compounds of Formula 17 can be prepared by reacting intermediate 3 witha compound Formula 16 in an appropriate solvent in the presence of abase. Thereafter intermediate 17 can be rearranged into the compound ofFormula 1g (i.e. Formula 1 wherein A is A-7) in the presence of a cyanocompound and a base as shown in Scheme 9. For reaction conditions forthis general coupling methodology, see Almisick A. V. in Modern CropProtection Compounds; Kramer, W. and Schirmer, U., Eds.; Wiley,Weinheim, 2007; Chapter 4.4, and references cited therein.

Compounds of Formula 19 can be prepared from corresponding compounds ofFormula 1g wherein R¹³ is an alkoxycarbonyl in the presence of an acidsuch as hydrogen chloride, sulfuric or acetic acid and optionally in thepresence of a solvent such as tetrahydrofuran, diethyl ether ordichloromethane as shown in Scheme 10. Intermediate 19 is then reactedwith an orthoformate ester or N,N-dimethylformamide dimethylacetal(DMF-DMA) in the presence of an acid to obtain intermediate 20. Reactionof intermediate 20 with hydroxylamine hydrochloride salt in a solventsuch as ethanol, acetonitrile, water or acetic acid provides isoxazolecompounds of Formula 1h (i.e. Formula 1 wherein A is A-6 and R¹¹ is H).For reaction conditions for this general cyclization methodology, seeAlmisick A. V. in Modern Crop Protection Compounds; Kramer, W. andSchirmer, U., Eds.; Wiley, Weinheim, 2007; Chapter 4.4, and referencescited therein.

As illustrated in Scheme 11, sulfoxides and sulfones of Formula 1wherein R² is a substituent bonded through a sulfoxide or sulfoneradical can be prepared by oxidation of the compounds of Formula 1wherein R² is a substituent bonded through a sulfide radical. In atypical procedure, an oxidizing agent in an amount from 1 to 4equivalents depending on the oxidation state of the product desired isadded to a solution of the compound of Formula 1 in a solvent. Usefuloxidizing agents include Oxone® (potassium peroxymonosulfate), hydrogenperoxide, sodium periodate, peracetic acid and 3-chloroperbenzoic acid.The solvent is selected with regard to the oxidizing agent employed.Aqueous ethanol or aqueous acetone is preferably used with potassiumperoxymonosulfate, and dichloromethane is generally preferable with3-chloroperbenzoic acid. Useful reaction temperatures typically rangefrom 0 to 90° C. Particular procedures useful for oxidizing sulfides tosulfoxides and sulfones are described by Brand et al., J. Agric. FoodChem. 1984, 32, 221-226 and references cited therein.

One skilled in the art will realize that acid chlorides of Formula 3d(i.e. Formula 3 wherein G¹ is Cl) are easily prepared from the acid ofFormula 6 (Scheme 12) by numerous well-known methods. For examplereacting the acid with a chlorinating reagent such as oxalyl chloride orthionyl chloride in a solvent such as dichloromethane or toluene andoptionally in the presence of a catalytic amount ofN,N-dimethylformamide can provide the corresponding acid chloride ofFormula 3d.

Compounds of Formula 6 can be prepared from esters of Formula 23 bynumerous well-known methods, for example standard saponificationprocedures using aqueous bases such as LiOH, NaOH or KOH in a solventsuch methanol or ethanol as described in Scheme 13. Alternatively, adealkylating agent such as lithium iodide or trimethylsilyl iodide canbe used in the presence of a base in a solvent such as pyridine or ethylacetate. Additional reaction procedures for deesterification can befound in PCT Patent Publication WO 2006/133242. Boron tribromide (BBr₃)can alternatively be used to to prepare a compound of Formula 6 from acompound of Formula 23 in a solvent such as dichloromethane. Proceduresusing boron tribromide can be found in Bioorg. & Med. Chem. Lett. 2009,19(16), 4733-4739.

Pyrimidinone esters of Formula 23a (i.e. Formula 23 wherein Alk isethyl, X is CH and Y is C(O)) are prepared as illustrated in Scheme 14by N-alkylation of pyridones of Formula 26 with agents such as alkylhalides in the presence of a base such as sodium hydride or potassiumcarbonate in a solvent such as N,N-dimethylformamide, tetrahydrofuran ordiethyl ether.

Pyrimidinone esters of Formula 23a can be made by the method of Scheme15. In this method an methylene malonate of Formula 28 is cyclized withan amidine salt of Formula 29 wherein X is a halogen or sulfonatecounter ion in the presence of excess base such as sodium alkoxide orpotassium carbonate in an appropriate solvent such as ethanol (generallyat the reflux temperature of the solvent) to give the correspondingpyrimidinone of Formula 3f. Examples of this synthetic method arereported in PCT Patent Publication WO 2006/133242 or Tetrahedron 2001,57, 2689.

Pyrimidinone esters of Formula 26 can be prepared by the method ofScheme 16. In this method, an ethylene malonate of Formula 28 iscyclized with an amidine salt Formula 29a wherein X is a halogen orsulfonate counter ion in the presence of excess base such as sodiumalkoxide or potassium carbonate in an appropriate solvent such asmethanol (generally at the reflux temperature of the solvent) to givethe corresponding pyrimidinone of Formula 26. Examples of this syntheticprocedure are reported in PCT Patent Publication WO 2006/133242,Tetrahedron 2001, 57, 2689.

Thiones of Formula 23b (i.e. Formula 23 wherein Alk is ethyl, X is CHand Y is S(O)₂) can be made by the method of Scheme 17. In this methodamidines of Formula 29 is reacted with acetal 30 in the presence of abase such as triethylamine, pyridine or potassium carbonate to give thecorresponding azabutadiene 31. Reacting this compound with the sulfonicacid chloride 32 as shown in Scheme 17 in the presence of a base such astriethylamine, pyridine or potassium carbonate in an appropriate solventresults in the corresponding compound of Formula 33. The correspondingthiones of formula 23b can be obtained by reacting the compound ofFormula 33 with iodomethane and subsequent treatment with a base such astriethylamine. Examples of this synthetic methodology are reported inSynthesis 2000, 5, 695.

Triazines of Formula 23c (i.e. Formula 23 wherein Alk is ethyl, X is Nand Y is C(O)) can be made by the method of Scheme 18. In this method aketomalonate of Formula 34 is cyclized with a semicarbazide of Formula29c wherein X is a halogen or sulfonate counter ion with or without thepresence of excess base such as sodium alkoxide or potassium carbonatein an appropriate solvent such as ethanol or t-butanol (generally at thereflux temperature of the solvent) to the corresponding triazine ofFormula 23c. Examples of this synthetic methodology are found in Eur. J.Med. Chem. 2008, 43(5), 1085, Bull. Soc. Chim. Fr. 1976, (11-12, Pt. 2),1825 and J. Org. Chem. 1962, 27, 976.

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula 1 may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula 1. One skilled in the artwill also recognize that it may be necessary to perform a combination ofthe steps illustrated in the above schemes in an order other than thatimplied by the particular sequence presented to prepare the compounds ofFormula 1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. Steps in the following Examples illustrate a procedure foreach step in an overall synthetic transformation, and the startingmaterial for each step may not have necessarily been prepared by aparticular preparative run whose procedure is described in otherExamples or Steps. Percentages are by weight except for chromatographicsolvent mixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹H NMR spectra are reported in ppm downfield fromtetramethylsilane at 400 MHz unless otherwise noted; “s” means singlet,“m” means multiplet, “br s” means broad singlet, “d” means doublet, “t”means triplet, “dt” means doublet of triplets, “q” means quartet and“sep” means septet.

Example 1 Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone(Compound 2) Step A: Preparation of N-phenylbenzenecarboximidamidesodium salt

To a stirred solution of sodium bis(trimethylsilyl)amide (1.0 M intetrahydrofuran, 21.5 mL, 21.5 mmol) in tetrahydrofuran (10 mL) wasadded aniline (2.0 g, 21.5 mmol) and allowed to stir for 10 min at roomtemperature. Benzonitrile (2.21 g, 21.5 mmol) was added, and thereaction mixture was stirred for 1 h at room temperature. The solid thatprecipitated was filtered, washed with diethyl ether and dried underreduced pressure to afford the title product as an off-white solid (4.0g), which was used without further purification in the next step.

Step B: Preparation of (A)1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid ethyl esterand (B) 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid

To a stirred solution of N-phenylbenzenecarboximidamide sodium salt(i.e. the product from Step A) (6.0 g, 27.5 mmol) in acetonitrile (30mL) was added ammonium chloride (1.47 g, 27.5 mmol) followed by diethylethoxymethylenemalonate (5.94 g, 27.5 mmol). The reaction mixture washeated and stirred at reflux for 2 h. The reaction mixture wasconcentrated under reduced pressure to give a residue. Water (30 mL) wasadded to the residue, followed by a saturated solution of sodiumbicarbonate (30 mL), and the mixture was extracted with ethyl acetate.The aqueous layer was separated and retained. The organic layer wasdried (MgSO₄) and concentrated under reduced pressure. The resultingresidue was purified by column chromatography eluting with 30% ethylacetate in hexanes to afford the title product (A) as a white solid(2.80 g).

¹H NMR (CDCl₃) δ 8.81 (s, 1H), 7.11-7.33 (m, 10H), 4.41 (m, 2H), 1.39(m, 3H).

The above retained aqueous layer was acidified with 1 N hydrochloricacid until the pH was 1-2, and the mixture was extracted withdichloromethane. The organic layer was dried (MgSO₄) and concentratedunder reduced pressure to provide a solid, which was washed with diethylether and dried under reduced pressure to afford the title product (B)as a white solid (680 mg).

¹H NMR (DMSO-d₆) δ 13.03 (s, 1H), 8.79 (s, 1H), 7.22-7.36 (m, 10H).

Step B1: Preparation of1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (alternatepreparation to Step B, product (B))

To a stirred solution of1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid ethyl ester(i.e. Step B product (A)) (2.30 g, 7.18 mmol) in pyridine (15 mL) wasadded lithium iodide (2.46 g, 18.0 mmol). The reaction mixture washeated to reflux with stirring for 24 h. The reaction mixture wasconcentrated under reduced pressure. To the resulting residue was addedwater (10 mL) followed by 1 N hydrochloric acid until the pH was 7. Thesolution was filtered though Celite® diatomaceous filter aid. Thefiltrate was acidified with 1 N hydrochloric acid until the pH was 1,and the mixture was extracted with dichloromethane. The organic layerwas dried (MgSO₄) and concentrated under reduced pressure to afford asolid, which was washed with diethyl ether and dried under reducedpressure to afford the title product as a white solid (1.40 g).

¹H NMR (DMSO-d₆) δ 13.03 (s, 1H), 8.79 (s, 1H), 7.22-7.36 (m, 10H).

Step C: Preparation of 3-oxo-1-cyclohexen-1-yl1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylate

To a stirred solution of1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylic acid (i.e. Step Bproduct (B) or the product from Step B1) (1.40 g, 4.8 mmol) indichloromethane (30 mL) was added oxalyl chloride (1.21 g, 9.61 mmol) at0° C. followed by catalytic amount (2 drops) of N,N-dimethylformamide.The reaction mixture was allowed to warm to room temperature and stirfor 1 h. Then the reaction mixture was concentrated under reducedpressure. To the resulting residue was added dichloromethane (30 mL),1,3-cyclohexanedione (646 mg, 5.76 mmol), followed by triethylamine (976mg, 9.60 mmol), and the reaction mixture was stirred at room temperaturefor 30 min. Saturated aqueous ammonium chloride solution was added, andthe mixture was extracted with dichloromethane. The organic layer wasdried (MgSO₄) and concentrated under reduced pressure. The residue waspurified by column chromatography eluting with 50% ethyl acetate inhexanes to afford the title product as a white solid (1.1 g).

¹H NMR (CDCl₃) δ 8.89 (s, 1H), 7.31-7.36 (m, 5H), 7.24-7.26 (m, 3H),7.12-7.15 (m, 2H), 6.04 (m, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.11 (m,2H).

Step D: Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone(Compound 2)

To a stirred solution of 3-oxo-1-cyclohexen-1-yl1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylate (i.e. the productfrom Step C) (640 mg, 1.65 mmol) in acetonitrile (20 mL) was addedtriethylamine (401 mg, 3.97 mmol), followed by a catalytic amount ofacetone cyanohydrin (3 drops). The reaction mixture was stirred for 24 hat room temperature and then concentrated under reduced pressure. To theresulting residue was added dichloromethane and 1 N hydrochloric acid.The organic layer was separated, and the aqueous layer was extractedwith dichloromethane. The combined organic layers were dried (MgSO₄) andconcentrated under reduced pressure. The residue was purified by columnchromatography eluting with 100% ethyl acetate to afford the titleproduct, a compound of the present invention, as a white solid (150 mg).

¹H NMR (CDCl₃) δ 8.24 (s, 1H), 7.12-7.34 (m, 10H), 2.70 (m, 2H), 2.48(m, 2H), 2.03 (m, 2H).

Example 2 Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone(Compound 17) Step A: Preparation ofN-(phenylmethyl)-benzenecarboximidamide

To a stirred solution of ethylbenzimidate hydrochloride (3.0 g, 16.2mmol) in N,N-dimethylformamide (10 mL) was added triethylamine (1.60 g,16.2 mmol). The reaction mixture was allowed to stir at room temperaturefor 1 h and then filtered to remove triethylamine salts, which wererinsed with N,N-dimethylformamide (5 mL). Benzylamine (1.23 g, 11.5mmol) was added to the filtrate, and the mixture was heated to 65° C.for 24 h. To the cooled mixture was added water (80 mL) and ethylacetate. The organic layer was washed with water and brine, then dried(MgSO₄) and concentrated under reduced pressure to afford the titleproduct as a clear oil (2.80 g).

¹H NMR (CDCl₃) δ 7.61 (m, 2H), 7.26-4.43 (m, 8H), 4.57 (m, 2H), 4.37 (m,1H), 1.42 (m, 1H).

Step B: Preparation of ethyl1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of N-(phenylmethyl)-benzenecarboximidamide (i.e.the product from Step A) (2.54 g, 12.1 mmol) in ethanol (15 mL) wasadded diethyl ethoxymethylenemalonate (2.61 g, 12.1 mmol), and thereaction mixture was heated to reflux for 24 h. The reaction mixture wasthen allowed to cool to room temperature and concentrated under reducedpressure. The residue was purified by column chromatography eluting with30% ethyl acetate in hexanes to afford the title product as a whitesolid (2.9 g).

¹H NMR (CDCl₃) δ 8.71 (s, 1H), 7.51 (m, 1H), 7.42 (m, 2H), 7.33 (m, 2H),7.23 (m, 3H), 6.93 (m, 2H), 5.28 (s, 2H), 4.42 (m, 2H), 1.40 (m, 3H).

Step C: Preparation of1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid

To a stirred solution of ethyl1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate(i.e. the product from Step B) (2.9 g, 8.6 mmol) in pyridine (15 mL) wasadded lithium iodide (3.01 g, 21.7 mmol). The reaction mixture washeated to reflux for 4 h, cooled, and then stirred at room temperaturefor 72 h. The reaction mixture was concentrated under reduced pressure.To the resulting residue was added water (10 mL), followed by 1 Nhydrochloric acid until the pH was 7. The solution was filtered throughCelite® diatomaceous filter aid, and the filtrate was acidified with 1 Nhydrochloric acid until the pH was 1. The mixture was extracted withdichloromethane, and the organic layer was dried (MgSO₄) andconcentrated under reduced pressure to afford a solid, which was washedwith diethyl ether and dried under reduced pressure to afford the titleproduct as a white solid (2.2 g).

Step D: Preparation of 3-oxo-1-cyclohexen-1-yl1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid(i.e. the product from Step C) (1.00 g, 3.26 mmol) in dichloromethane(30 mL) at 0° C., was added oxalyl chloride (823 mg, 6.53 mmol) followedby a catalytic amount of N,N-dimethylformamide (2 drops). The reactionmixture was allowed to warm to room temperature and stir for 1 h. Thenthe reaction mixture was concentrated under reduced pressure. To theresulting residue was added dichloromethane (30 mL) and1,3-cyclohexanedione (440 mg, 3.90 mmol), followed by triethylamine (990mg, 9.80 mmol), and the reaction mixture was stirred at room temperaturefor 30 min Saturated aqueous ammonium chloride solution was added to thereaction mixture, which was then extracted with dichloromethane. Theorganic layer was dried (MgSO₄) and concentrated under reduced pressure.The residue was purified by column chromatography eluting with 50% ethylacetate in hexanes to afford the title product as a white solid (500mg).

¹H NMR (CDCl₃) δ 8.81 (s, 1H), 7.55 (m, 1H), 7.45 (m, 2H), 7.37 (m, 2H),7.25 (m, 3H), 6.95 (m, 2H), 6.03 (s, 1H), 5.30 (s, 2H), 2.69 (m, 2H),2.46 (m, 2H), 2.12 (m, 2H).

Step E: Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone(Compound 17)

To a stirred solution of 3-oxo-1-cyclohexen-1-yl1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate(i.e. the product from Step D) (450 mg, 1.12 mmol) in acetonitrile (15mL) was added triethylamine (272 mg, 2.69 mmol), followed by a catalyticamount (3 drops) of acetone cyanohydrin. The reaction mixture wasstirred for 24 h at room temperature and then concentrated under reducedpressure. To the resulting residue were added dichloromethane and 1 Nhydrochloric acid, and the aqueous layer was extracted withdichloromethane. The organic layer was dried (MgSO₄) and concentratedunder reduced pressure. The residue was purified by columnchromatography eluting with ethyl acetate to afford the title product, acompound of the present invention, as a white solid (160 mg).

¹H NMR (CDCl₃) δ 16.44 (br s, 1H), 8.17 (s, 1H), 7.47 (m, 1H), 7.37 (m,2H), 7.21-7.30 (m, 5H), 6.95 (m, 2H), 5.20 (s, 2H), 2.72 (m, 2H), 2.51(m, 2H), 2.06 (m, 2H).

Example 3 Preparation of5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone(Compound 20) Step A: Preparation of 1-ethyl-1H-pyrazol-5-yl1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate

To a stirred solution of1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylic acid(i.e. the product from Example 2, Step C) (1.20 g, 3.92 mmol) indichloromethane (30 mL) was added oxalyl chloride (998 mg, 7.84 mmol) at0° C. followed by a catalytic amount (4-drops) of N,N-dimethylformamide.The reaction mixture was allowed to warm to room temperature and stirfor 1 h. The reaction mixture was then concentrated under reducedpressure. To the resulting residue was added dichloromethane (30 mL) and5-hydroxy-1-ethyl-1H-pyrazole, (572 mg, 4.7 mmol), followed bytriethylamine (1.18 g, 11.8 mmol), and the reaction mixture was stirredat room temperature for 30 min. Saturated aqueous ammonium chloridesolution was added to the reaction mixture, which was then extractedwith dichloromethane. The organic layer was dried (MgSO₄) andconcentrated under reduced pressure. The residue was purified by columnchromatography eluting with 70% ethyl acetate in hexanes to afford thetitle product as a white solid (700 mg).

¹H NMR (CDCl₃) δ 8.90 (s, 1H), 7.56 (m, 1H), 7.46 (m, 3H), 7.38 (m, 2H),7.26 (m, 3H), 6.95 (m, 2H), 6.29 (m, 1H), 5.34 (s, 2H), 4.19 (m, 2H),1.45 (m, 3H).

Step B: Preparation of5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone(Compound 20)

To a stirred solution of 1-ethyl-1H-pyrazol-5-yl1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate(i.e. the product from Step A) (650 mg, 1.62 mmol) in acetonitrile (15mL) was added triethylamine (393 mg, 3.70 mmol), followed by a catalyticamount (5 drops) of acetone cyanohydrin. The reaction mixture wasstirred for 24 h at room temperature and then concentrated under reducedpressure. To the residue were added dichloromethane and 1 N hydrochloricacid, and the aqueous layer was extracted with dichloromethane. Theorganic layer was dried (MgSO₄) and concentrated under reduced pressure.The residue was purified by column chromatography eluting with 10%methanol in ethyl acetate to afford the title product, a compound of thepresent invention, as a white solid (150 mg).

¹H NMR (CDCl₃) δ 8.56 (s, 1H), 7.86 (s, 1H), 7.53 (m, 1H), 7.39-7.46 (m,4H), 7.24 (m, 3H), 6.97 (m, 2H), 5.33 (s, 2H), 4.04 (m, 2H), 1.42 (m,3H).

Example 4 Step A: Preparation of5-[[1-ethyl-5-[[(4-methylphenyl)sulfonyl]oxy]-1H-pyrazol-4-yl]carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone(Compound 21)

To a stirred solution of5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone(i.e. the product from Example 3, Step B) (300 mg, 0.75 mmol) inacetonitrile (10 mL) was added triethylamine (116 mg, 1.12 mmol),followed by p-toluenesulfonyl chloride (171 mg, 0.90 mmol), and thereaction mixture was stirred at room temperature for 72 h. Saturatedaqueous ammonium chloride solution was added to the mixture, and theaqueous layer was extracted with dichloromethane. The organic layer wasdried (MgSO₄) and concentrated under reduced pressure. The residue waspurified by column chromatography eluting with 50% ethyl acetate inhexanes to afford the title product, a compound of the presentinvention, as a white solid (160 mg).

¹H NMR (CDCl₃) δ 8.07 (s, 1H), 7.84 (s, 1H), 7.74 (m, 2H), 7.44 (m, 2H),7.25-7.35 (m, 8H), 6.95 (m, 2H), 5.23 (s, 2H), 4.00 (m, 2H), 2.41 (s,3H), 1.42 (m, 3H).

Example 5 Preparation of3-(3-fluoro-2-methylphenyl)-5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone(Compound 47) Step A: Preparation ofN-(3-fluoro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1)

To a stirred solution of sodium bis(trimethylsilyl)amide (1.0 M intetrahydrofuran, 200.0 mL, 200.0 mmol) was added3-fluoro-2-methylaniline (25.0 g, 200.0 mmol) and allowed to stir for 10min at room temperature. Benzonitrile (20.6 g, 200.0 mmol) was added,and the reaction mixture was stirred for 1 h at room temperature. Thereaction mixture was concentrated and the solid that formed wasfiltered, washed with diethyl ether and dried under reduced pressure toafford the title product as a grey solid (51.0 g), which was usedwithout further purification in the next step.

Step B: Preparation of1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylicacid

To a stirred solution ofN-(3-fluoro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1)(i.e. the product from Example 5, Step A) (51.0 g, 200 mmol) inacetonitrile (300 mL) was added diethyl ethoxymethylenemalonate (44.04g, 200 mmol). The reaction was stirred at room temperature for 30 minfollowed by the addition of water (3.6 mL, 200 mmol). The reaction wasthen stirred for another 30 min Water (100 mL) was added to the residue,followed by a saturated solution of sodium bicarbonate (300 mL), and themixture was extracted with ethyl acetate. The aqueous layer wasacidified with concentrated hydrochloric acid until the pH was 1-2, andthe mixture was extracted with dichloromethane. The organic layer wasdried (MgSO₄) and concentrated under reduced pressure to provide asolid, which was washed with diethyl ether and dried under reducedpressure to afford the title product as a off-white solid (18 g).

¹H NMR (CDCl₃) δ 12.68 (s, 1H), 9.15 (s, 1H), 7.43 (m, 1H), 7.19-7.38(m, 5H), 7.12 (m, 1H), 6.88 (m, 1H), 2.03 (s, 3H).

Step C: Preparation of 3-oxo-1-cyclohexen-1-yl1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate

To a stirred solution of1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylicacid (i.e. the product from Example 5, Step B) (41.0 g, 126 mmol) indichloromethane (400 mL) was added oxalyl chloride (31.05 g, 252.0 mmol)at 0° C. followed by a catalytic amount (7 drops) ofN,N-dimethylformamide. The reaction mixture was allowed to warm to roomtemperature and stir for 1 h. The reaction mixture was then concentratedunder reduced pressure. To the resulting residue was addeddichloromethane (400 mL), 1,3-cyclohexanedione (17.03 g, 152 mmol),followed by triethylamine (38.30 g, 379 mmol) and the reaction mixturewas stirred at room temperature for 30 min. Saturated aqueous ammoniumchloride solution was added, and the mixture was extracted withdichloromethane. The organic layer was washed once with water. Then theorganic layer was dried (MgSO₄) and concentrated under reduced pressure.The resulting solid was washed with chlorobutane to afford the titleproduct pure as an off-white solid (37.6 g).

¹H NMR (CDCl₃) δ 8.92 (s, 1H), 7.24-7.40 (m, 5H), 7.18 (m, 1H), 7.05 (m,1H), 6.87 (m, 1H), 6.05 (s, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.11 (m,2H), 2.03 (s, 3H).

Step D: Preparation of3-(3-fluoro-2-methylphenyl)-5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)-carbonyl]-2-phenyl-4(3H)-pyrimidinone

To a stirred solution of 3-oxo-1-cyclohexen-1-yl1-(3-fluoro-2-methylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate(i.e. the product from Example 5, Step C) (42 g, 100.4 mmol) inacetonitrile (200 mL) was added cesium fluoride (30.5 g, 200.8 mmol).The reaction mixture was stirred for 24 h at room temperature. Water andethyl acetate was added to the reaction mixture and the water layer wasextracted several times with ethyl acetate. The combined organic layerswere dried (MgSO₄) and concentrated under reduced pressure. Theresulting solid was washed several times with ether and filtered,followed by the addition 60 mL of ethyl acetate and let stir for 2 h.The resulting solid was then washed again with ether and dried underreduced pressure to afford the title product, a compound of the presentinvention, as a yellow solid (26 g).

¹H NMR (CDCl₃) δ 16.38 (s, 1H), 8.28 (s, 1H), 7.21-7.34 (m, 5H), 7.11(m, 1H), 7.00 (m, 1H), 6.86 (m, 1H), 2.70 (m, 2H), 2.47 (m, 2H), 2.10(m, 3H), 2.03 (m, 2H).

Example 6 Preparation of5-[(5-cyclopropyl-4-isoxazolyl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone(Compound 223) Step A: Preparation of1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-1,3-propanedione

To a mixture of 1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinecarboxylicacid (i.e. the product from Example 1, step B) (1.84 g, 6.3 mmol) andtoluene (6.3 mL) was added phosphorus pentachloride (1.31 g, 6.3 mmol)at ambient temperature. The resulting mixture was heated at reflux undera nitrogen atmosphere for 6 h. The resulting yellow solution wasconcentrated to give 1.53 g of the acid chloride as a yellow solid.

n-Butyllithium (2.5M solution in hexanes, 2.2 mL, 5.6 mmol) was addeddropwise to a solution of N,N-diisopropylamine (0.82 mL, 5.8 mmol) andanhydrous tetrahydrofuran (8 mL) at −78° C. under a nitrogen atmosphere.The resulting solution was warmed to 0° C., stirred for 30 min, and thencooled to −78° C. Cyclopropyl methyl ketone (0.55 mL, 5.6 mmol) wasadded dropwise at below −65° C. The resulting solution was stirred at−78° C. for 30 min and was then treated with a slurry of the acidchloride as prepared above (823 mg, 2.7 mmol) in anhydroustetrahydrofuran (5 mL) added dropwise via syringe at below 60° C.Additional anhydrous tetrahydrofuran (5 mL) was used to complete thetransfer of the acid chloride. The resulting mixture was stirred at −78°C. for 1 h and was then treated with saturated aqueous ammonium chloride(7 mL) at below −50° C. The resulting mixture was stirred at ambienttemperature for 15 min and was partitioned between ethyl acetate (100mL) and saturated aqueous ammonium chloride (50 mL). The organic layerwas dried over MgSO₄, filtered, and concentrated onto silica gel (2.5g). The residue was purified by medium pressure liquid chromatographyusing a 24 g silica column and eluting with a gradient of 0 to 100%ethyl acetate in hexanes to provide the title compound as a pale yellowglassy solid (250 mg).

¹HNMR (400 MHz, CDCl₃) δ 15.88 (s, 1H), 8.93 (s, 1H), 7.40-7.33 (m, 3H),7.33-7.26 (m, 3H), 7.24-7.19 (m, 3H), 7.14 (apparent d, 2H), 1.81 (sep,1H), 1.20-1.15 (m, 2H), 0.99-0.92 (m, 2H).

Step B: Preparation of1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-2-(ethoxymethylene)-1,3-propanedione

A suspension of1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-1,3-propanedione(i.e. the product from Example 6, Step A) (165 mg, 0.46 mmol), triethylorthoformate (0.23 mL, 1.4 mmol), and acetic anhydride (0.92 mL) washeated at 110° C. under a nitrogen atmosphere for 4 h. The residue wasdissolved in toluene (5 mL) and the resulting solution was concentratedunder reduced pressure at 50° C. The residue was re-dissolved in toluene(5 mL) and the resulting solution was concentrated at 50° C. to give 181mg of the title compound as a brown oil that was used in the next stepwithout further purification. ¹H NMR analysis showed the product tocontain a mixture of Z- and E-olefin isomers.

¹HNMR (400 MHz, CDCl₃) 8.63 and 8.47 (2s, 1H total), 7.68 and 7.62 (2s,1H total), 7.33-7.16 (m, 8H), 7.10-7.02 (m, 2H), 4.27 and 4.16 (2q, 2Htotal), 2.64-2.57 (m, <1H), 1.42 and 1.33 (3t, 3H total), 1.11-1.06 and1.04-0.98 (2m, 2H total), 0.91-0.82 (m, 2H).

Step C: Preparation of5-[(5-cyclopropyl-4-isoxazolyl)carbonyl]-2,3-diphenyl-4(3H)-pyrimidinone

Anhydrous sodium acetate (68 mg, 0.83 mmol) was added to a solution of1-cyclopropyl-3-(1,6-dihydro-6-oxo-1,2-diphenyl-5-pyrimidinyl)-2-(ethoxymethylene)-1,3-propanedione(i.e. the product from Example 6, Step B) (171 mg, 0.41 mmol) in ethanol(4 mL) at 0° C. Hydroxylamine hydrochloride (29 mg, 0.42 mmol) was addedand the resulting suspension was stirred at 0° C. for 30 min and then atambient temperature for 2 h. The resulting mixture was diluted withethyl acetate (20 mL) and ethanol (20 mL), concentrated onto 0.8 gsilica gel, and the residue purified by medium pressure liquidchromatography using a 12 g silica gel column and eluting with 0 to 100%ethyl acetate in hexanes to obtain 14 mg of the title compound, acompound of the present invention as a yellow glassy solid.

¹HNMR (400 MHz, CDCl₃) 8.56 (s, 1H), 8.45 (s, 1H), 7.40-7.30 (m, 6H),7.25-7.20 (m, 2H), 7.16-7.12 (m, 2H), 3.02-2.93 (m, 1H), 1.37-1.32 (m,2H), 1.27-1.22 (m, 2H).

Example 7 Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-phenyl-2-(3-pyridinyl)-4(3H)-pyrimidone(Compound 113) Step A: Preparation of N-phenyl-3-pyridinecarboximidamide

Sodium hydride (60% in mineral oil, 11.52 g, 288 mmol) was addedportion-wise over 30 min to a stirred solution of 3-pyridinecarbonitrile(30 g, 288 mmol) and aniline (26 g, 290 mmol) in dimethylsulfoxide (150mL) at 10° C. The reaction mixture was allowed to warm to ambienttemperature with stirring for 18 h. The reaction mixture was slowly andcautiously poured into water containing crushed ice. The solid thatprecipitated was filtered, washed with petroleum ether, dissolved indichloromethane and dried over anhydrous Na₂SO₄. The volatiles wereremoved under reduced pressure (high vacuum) and the residue was driedto afford 36.5 g of the title compound as a yellow solid.

¹H NMR (CDCl₃, 500 MHz) δ 9.06 (s, 1H), 8.68 (d, 1H), 8.22 (d, 1H),7.38-7.35 (m, 3H), 7.08 (t, 1H), 6.97 (d, 2H), 5.00 (s, 2H).

Step B: Preparation of ethyl1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate

A suspension of the N-phenyl-3-pyridinecarboximidamide (i.e. the productfrom Example 7, Step A) (36.5 g, 185 mmol) in diethylethoxymethylenemalonate (60 g, 280 mmol) was heated to 160° C. for 8 h.Ethanol formed in the reaction was collected using a distillation headattached to the flask containing the heated reaction mixture. Thereaction mixture was then cooled to ambient temperature when theformation of a solid was observed. A mixture of diethyl ether/petroleumether (8:2) was added to the reaction mixture was filtered. Thecollected solid was washed with additional ether/petroleum ether (4:1)followed by n-chlorobutane/petroleum ether (1:1) to obtain 51 g of thetitle compound as a light brown powder.

¹H NMR (CDCl₃, 500 MHz) δ 8.79 (s, 1H), 8.57 (dd, 1H), 8.52 (dd, 1H),7.58 (dt, 1H), 7.38-7.35 (m, 3H), 7.16-7.13 (m, 3H), 4.41 (q, 2H), 1.39(t, 3H).

Step C: Preparation of1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylic acid

A suspension of ethyl1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate (i.e.the product from Example 7, Step B) (5.0 g, 15.5 mmol) and lithiumiodide (powder, 5.2 g, 38.8 mmol) in pyridine (15 mL) was heated to125-130° C. for 12 h. After cooling to ambient temperature, excesssolvent was removed under reduced pressure. The resulting residue wasdissolved in water (100 mL) and acidified with hydrochloric acid (6 N)to pH 7. The resulting dark brown solution was extracted with ethylacetate (1×100 mL) to remove the non polar impurities. The aqueous layerwas again extracted with dichloromethane/methanol (95:5) (2×50 mL).After initial extractions, the aqueous layer was slowly acidified to pH4 and further extracted with dichloromethane/methanol (95:5) (3×50 mL).The combined neutral and acidic extracts were washed with brine anddried over anhydrous Na₂SO₄. The residue obtained after removal of thesolvent was dried under high-vacuum to obtain 3.4 g of the titlecompound as a light brown solid.

¹H NMR (CDCl₃, 500 MHz) δ 12.67 (br s, 1H), 9.12 (s, 1H), 8.60-8.57 (m,2H), 7.65 (dt, 1H), 7.47-7.46 (m, 3H), 7.22-7.19 (m, 3H).

Step D: Preparation of 3-oxo-1-cyclohexen-1-yl1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate

To a stirred suspension of1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylic acid(i.e. the product from Example 7, Step C) (10.7 g, 36.3 mmol) indichloromethane (150 mL) at ambient temperature was added2-chloro-N-methyl pyridinium iodide (also known as the Mukaiyamareagent) (14.8 g, 57.9 mmol) followed by cyclohexanedione (6.5 g, 58mmol) and triethylamine (9.2 g, 91 mmol). The reaction mixture was leftstirring at ambient temperature overnight, then diluted withdichloromethane, washed with water, brine and dried over anhydrousNa₂SO₄. The residue obtained after removal of the solvent under vacuumwas purified by tituration with n-chlorobutane/petroleum ether mixturesto obtain 9.8 g of the title compound as a light brown solid.

¹H NMR (CDCl₃, 500 MHz) δ 8.89 (s, 1H), 8.60 (d, 1H) 8.54 (dd, 1H), 7.61(dt, 1H), 7.42-7.37 (m, 3H), 7.19-7.14 (m, 3H), 6.04 (s, 1H), 2.69-2.66(m, 2H), 2.45-2.42 (m, 2H), 2.10 (q, 2H).

Step E: Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-phenyl-2-(3-pyridinyl)-4(3H)-pyrimidone

To a stirred solution of 3-oxo-1-cyclohexen-1-yl1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate (i.e.the product from Example 7, Step D) (11.1 g, 28.6 mmol) in acetonitrile(166 mL) was added cesium fluoride (8.71 g, 57.3 mmol) followed bycatalytic amount (˜50 mg) of tetrabutylammonium bromide at ambienttemperature. After stirring for 3 h at ambient temperature, the reactionmixture was diluted with ethyl acetate, washed with water, brine anddried over anhydrous Na₂SO₄. The volatile components were removed underreduced pressure and the residue was subjected to silica gel columnchromatography eluting with ethyl acetate/petroleum ether (1:1) to ethylacetate to dichloromethane/methanol (95:5). The product obtained waswashed with minimum amount of methanol to afford 1.4 g of the titlecompound, a compound of the present invention as a light yellow solid.

¹H NMR (CDCl₃, 500 MHz) mixture of tautomers δ 16.45 (s, 0.8H),8.57-8.50 (m, 2H), 8.21 (s, 1H), 7.57 (d, 1H), 7.35 (d, 3H), 7.16-7.13(m, 3H), 5.29 (s, 0.2H,), 2.71 (br s, 2H), 2.47 (br s, 2H), 2.04-2.02(m, 2H).

Example 8 Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone(Compound 168) and5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone(Compound 169) Step A: Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinoneand5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-4(3H)-pyrimidinone

To5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-3-(tetrahydro-2H-thiopyran-4-yl)-4(3H)-pyrimidinone(the tautomer known as2-[[1,6-dihydro-6-oxo-2-phenyl-1-(tetrahydro-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione)(0.15 g, 0.37 mmol) in a mixture of 5.0 mL water and 5.0 mL methanol atroom temperature was added NaIO₄ (0.074 g, 0.35 mmol). Afterapproximately 45 min, additional NaIO₄ (0.011 g, 0.05 mmol) was addedand stirring was continued for an additional 2 h. The reaction mixturewas extracted with dichloromethane and the combined organics were driedover MgSO₄ concentrated under reduced pressure and purified by mediumpressure liquid chromatography on silica gel eluting with 0 to 10%methanol in chloroform to provide 0.07 g of Compound 168 (alternativelyknown as2-[[1,6-dihydro-6-oxo-2-phenyl-1-(cis/trans-tetrahydro-1-oxido-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione)and and 0.03 g of Compound 169 (alternatively known as2-[[1,6-dihydro-6-oxo-2-phenyl-1-(trans/cis-tetrahydro-1-oxido-2H-thiopyran-4-yl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione)both as solids.

¹H NMR of Compound 168 (CDCl₃) δ16.58 (br s, 1H), 7.99 (s, 1H), 7.58 (m,3H), 7.47 (m, 2H), 4.14 (m, 1H), 3.39 (m, 2H), 3.12 (m, 2H), 2.74 (t,2H), 2.49 (t, 2H), 2.37 (t, 2H), 2.05 (m, 4H).

¹H NMR Compound 169 (CDCl₃) δ16.42 (br s, 1H), 8.00 (s, 1H), 7.54 (m,5H), 4.06 (m, 1H), 3.65 (m, 2H), 3.07 (m, 2H), 2.60 (br s, 4H), 2.17 (m,2H), 2.07 (m, 2H), 1.80 (d, 2H).

Example 9 Preparation of2-(3,5-difluorophenyl)-5-[(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl]-3-(2-methoxyethyl)-4(3H)-pyrimidinone(Compound 243) Step A: Preparation of 3,5-difluorobenzenecarboxamidicacid ethyl ester hydrochloride (1:1)

To a stirred solution of 3,5-difluorobenzonitirile (25 g, 180 mmol) inethanol (336 mL) and dichloromethane (180 mL) at 0° C., was added acetylchloride (128 mL, 1800 mmol) drop wise via addition funnel. The reactionmixture was allowed to warm to room temperature and stir for 24 h. Thereaction mixture was then concentrated under reduced pressure to afforda solid, which was washed with diethyl ether and dried under reducedpressure to afford the title product as a white solid (21.5 g) which wascarried forward to the next step without further purification.

Step B: Preparation of3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride(1:1)

To a stirred solution of 3,5-difluorobenzenecarboxamidic acid ethylester hydrochloride (5.39 g, 24.3 mmol) (i.e. the product from Example9, Step A) in methanol (25 mL) at 0° C., was added2-methoxy-1-ethylamine (2.2 mL, 25.5 mmol). The reaction mixture wasallowed to warm to room temperature and stir for 24 h. The reactionmixture was concentrated under reduced pressure to afford the titleproduct as a gummy oil, which was used without further purification inthe next step.

Step C: Preparation of ethyl2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxyate

To a stirred solution of3,5-difluoro-N-(2-methoxyethyl)benzenecarboximidamide hydrochloride (1:1(i.e. the product from Example 9, Step B) (24.3 mmol) in ethanol (25 mL)was added diethyl ethoxymethylenemalonate (5.25 g, 24.3 mmol) followedby sodium ethoxide (21% soln) (9.1 mL, 24.3 mmol). The reaction mixturewas heated and stirred at reflux for 24 h. The reaction mixture wascooled to room temperature concentrated under reduced pressure. Theresidue was purified by column chromatography eluting with 50% ethylacetate in hexanes to afford the title product as a white solid (6.1 g).

¹H NMR (CDCl₃) δ 8.65 (s, 1H), 7.14 (m, 2H), 6.98 (m, 1H), 4.41 (m, 2H),4.21 (m, 2H), 3.67 (m, 2H), 3.22 (s, 3H), 1.40 (m, 3H).

Step D: Preparation of2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylicacid

To a stirred solution of ethyl ethyl2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxyate(i.e. the product from Example 9, Step C) (1.14 g, 3.37 mmol) in ethylacetate (10 mL) was added lithium iodide powder (1.35 g, 10.0 mmol). Thereaction mixture was heated to reflux for 24 h, cooled, and then stirredat room temperature for 72 h. The reaction mixture was concentratedunder reduced pressure. To the resulting residue was added water (10mL), followed by 6 N hydrochloric acid until the pH was 2. The mixturewas extracted with dichloromethane, and the organic layer was dried(MgSO₄) and concentrated under reduced pressure to afford a solid, whichwas washed with diethyl ether and dried under reduced pressure to affordthe title product as a white solid (700 mg).

¹H NMR (CDCl₃) δ 12.88 (s, 1H), 8.99 (s, 1H), 7.20 (m, 2H), 7.03 (m,1H), 4.32 (m, 2H), 3.69 (m, 2H), 3.25 (s, 3H).

Step E: Preparation of2-(3,5-difluorophenyl)-5-[(2-hydroxy-4-oxobicyclo[3.2.1]oct-2-en-3-yl)carbonyl]-3-(2-methoxyethyl)-4(3H)-pyrimidinone

To2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinecarboxylicacid (i.e. the product from Example 9, Step D) (0.25 g, 0.81 mmol) in 10mL of dichloromethane was added oxalyl chloride (0.21 g, 1.6 mmol) andone drop of N,N-dimethylformamide. The reaction mixture was stirred atroom temperature for 2 h and then concentrated under reduced pressure.The remaining crude oil was re-dissolved in dichloromethane (10 mL) andthen treated with bicycle[3.2.1]octane-2,4-dione (0.12 g, 0.88 mmol)(prepared according to U.S. Pat. No. 6,815,563) and triethylamine (0.16g, 1.6 mmol). After 30 min at room temperature, a catalytic amount of2-hydroxy-2-methyl-propanenitrile (0.0075 g, 0.088 mmol) andtriethylamine (0.16 g, 1.6 mmol) were added and the reaction mixture wasstirred at ambient temperature over night. The reaction mixture was thenconcentrated under reduced pressure and purified by medium pressureliquid chromatography on silica gel eluting with 0 to 10% methanol inchloroform to provide 0.180 g of the title compound (also known as3-[[2-(3,5-difluorophenyl)-1,6-dihydro-1-(2-methoxyethyl)-6-oxo-5-pyrimidinyl]carbonyl]biciclo[3.2.1]octane-2,4-dione),a compound of the present invention, as a solid.

¹H NMR (CDCl₃) δ 16.58 (br s, 1H), 8.05 (s, 1H), 7.17 (m, 2H), 6.96 (m,1H), 4.18 (br s, 2H), 3.61 (t, 2H), 3.26 (br s, 3H), 3.09 (br s, 1H),2.96 (br s, 1H), 2.26 (d, 1H), 2.17 (br s, 2H), 2.02 (br s, 1H), 1.88(br s, 1H), 1.73 (m, 1H).

Example 10 Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone(Compound 97) Step A: Preparation of 3-thiophenecarboximidic acid ethylester hydrochloride

To a solution of thiophene-3-carbonitrile (10 g, 9.2 mmol) indichloromethane (100 mL) and ethanol (170 mL) at 0° C. was added acetylchloride (114 g, 145 mmol). The reaction was allowed to slowly warm toambient temperature and stir 16 h. The reaction mixture was thenconcentrated under reduced pressure to yield a solid which wastriturated with diethyl ether resulting in 17.1 g of3-thiophenecarboximidic acid ethyl ester hydrochloride as a white solid.

¹H NMR (DMSO-d₆) δ 11.77 (br s, 2H), 8.92 (m, 1H), 7.90 (m, 1H), 7.83(m, 1H), 4.60 (q, 2H), 1.46 (t, 3H).

Step B: Preparation of ethyl1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylate

2-Methoxy-1-ethylamine (0.86 g, 11.4 mmol) was added to a solution of3-thiophenecarboximidic acid ethyl ester hydrochloride (2.0 g, 10.4mmol) in methanol (10 mL), which was then stirred at ambient temperaturefor 1.5 h. The reaction mixture was then concentrated under reducedpressure and redissolved in ethanol (10 mL). Sodium ethoxide solution(21% w/w in ethanol, 3.4 g, 10 mmol) and diethyl ethoxymethylenemalonate(2.2 g, 10 mmol) were added and the mixture was heated to reflux for 2 hbefore being concentrated under reduced pressure and purified by mediumpressure liquid chromatography on silica gel eluting with 0 to 100%ethyl acetate in hexanes to provide 1.82 g of the title compound as anoil.

¹H NMR (CDCl₃) δ 8.68 (s, 1H), 8.06 (m, 1H), 7.48 (m, 1H), 7.43 (m, 1H),4.38 (m, 4H), 3.81 (t, 2H), 3.29 (s, 3H), 1.40 (t, 3H).

Step C:1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylicacid

Ethyl1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylatea (1.82 g, 5.90 mmol) (i.e. the product from Example 10, Step B) wasdissolved in ethyl acetate and treated with lithium iodide (powder, 2.36g, 17.6 mmol) and heated to reflux for 16 h. The crude reaction mixturewas concentrated under reduced pressure and then aqueous sodiumbicarbonate solution was added and the resulting solution was extractedwith ethyl acetate which was then discarded. The aqueous layer was madeacidic with hydrochloric acid (1 N) and then extracted withdichloromethane (2×40 mL). The combined organics were dried over MgSO₄and concentrated under reduced pressure to provide the title compound asa solid.

¹H NMR (CDCl₃) δ 12.96 (br s, 1H), 8.99 (s, 1H), 8.17 (m, 1H), 7.53 (m,1H), 7.48 (m, 1H), 4.47 (t, 2H), 3.83 (t, 2H), 3.32 (s, 3H).

Step D: Preparation of5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-3-(2-methoxyethyl)-2-(3-thienyl)-4(3H)-pyrimidinone

To1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylicacid (i.e. the product from Example 10, Step C) (0.5 g, 1.8 mmol) in 10mL of dichloromethane was added oxalyl chloride (0.45 g, 3.6 mmol) andone drop of N,N-dimethylformamide. The reaction mixture was stirred atroom temperature for 2 h and then concentrated under reduced pressure.The crude oil was redissolved in 10 mL of dichloromethane and treatedwith 1,3-cyclohexanedione (0.22 g, 2.0 mmol) and triethylamine (0.18 g,1.8 mmol). The reaction mixture was stirred for 30 min then treated witha catalytic amount of 2-hydroxy-2-methyl-propanenitrile (0.015 g, 0.18mmol) and triethylamine (0.182 g, 1.8 mmol) and stirred at ambienttemperature for 16 h. The reaction mixture was then concentrated underreduced pressure and purified by medium pressure liquid chromatographyon silica gel eluting with 0 to 10% methanol in chloroform to provide0.160 g of the title compound (also known as2-[[1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinyl]carbonyl]-1,3-cyclohexanedione),a compound of the invention, as a solid.

¹H NMR (CDCl₃) δ 16.51 (s, 1H), 8.14 (s, 1H), 7.97 (m, 1H), 7.43 (m,2H), 4.29 (t, 2H), 3.70 (t, 2H), 3.29 (s, 3H), 2.73 (t, 2H), 2.50 (t,2H), 2.08 (m, 2H).

Example 11 Preparation of3-cyclohexyl-5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-phenyl-4(3H)-pyrimidinone(Compound 128) Step A: Preparation of ethyl1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxyate

Cyclohexylamine (0.58 g, 5.8 mmol) was added to a solution of ethylbenzenecarboximidic acid ethyl ester (1.0 g, 5.4 mmol) in methanol (10mL), which was then stirred at room temperature for 16 h. The reactionmixture was then concentrated under reduced pressure and thenredissolved in ethanol (10 mL). Sodium ethoxide solution (21% w/w inethanol, 1.8 g, 5.5 mmol) and diethyl ethoxymethylenemalonate (1.2 g,5.5 mmol) were added and the mixture was heated to reflux for 16 hbefore being concentrated under reduced pressure and purified by mediumpressure liquid chromatography on silica gel eluting with 0 to 100%ethyl acetate in hexanes to provide 1.41 g of the title compound as ayellow oil.

¹H NMR (CDCl₃) δ 8.58 (s, 1H), 7.53 (m, 3H), 7.45 (m, 2H), 4.41 (m, 2H),3.94 (m, 1H), 2.76 (m, 2H), 1.78 (d, 2H), 1.67 (d, 2H), 1.53 (d, 1H),1.42 (m, 3H), 1.21 (m, 1H), 0.96 (m, 2H).

Step B: Preparation of1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid

Ethyl 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxyate(1.41 g, 4.32 mmol) (i.e. the product from Example 11, Step A) wasdissolved in ethyl acetate and treated with lithium iodide (powder, 1.72g, 12.8 mmol) and heated to reflux for 16 h. The crude reaction mixturewas concentrated under reduced pressure and then aqueous sodiumbicarbonate was added and the resulting solution was extracted withethyl acetate which was then discarded. The aqueous layer was madeacidic with hydrochloric acid (1 N) and then extracted withdichloromethane (2×40 mL). The combined organic extracts were dried overMgSO₄ and concentrated under reduced pressure resulting in 0.58 g of thetitle product as a solid.

¹H NMR (CDCl₃) δ 13.30 (br. s., 1H), 8.94 (s, 1H), 7.59 (m, 3H), 7.48(m, 2H), 4.12 (m, 1H), 2.68 (m, 2H), 1.84 (d, 2H), 1.74 (d, 2H), 1.60(d, 1H), 1.22 (m, 1H), 1.03 (m, 2H).

Step C: Preparation of2-[(1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinyl)carbonyl]-1,3-cyclohexanedione

To 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylic acid(i.e. the product from Example 11, Step B) (0.58 g, 1.5 mmol) in 10 mLof dichloromethane was added oxalyl chloride (0.490 g, 3.9 mmol) and onedrop of N,N-dimethylformamide. The reaction was stirred at ambienttemperature for 2 h and then concentrated under reduced pressure. Thecrude oil was then redissolved in 10 mL of dichloromethane and thentreated with 1,3-cyclohexanedione (0.24 g, 2.1 mmol) and triethylamine(0.39 g, 3.8 mmol) stirred for 30 min, then treated with a catalyticamount of 2-hydroxy-2-methyl-propanenitrile (0.015 g, 0.15 mmol) andtriethylamine (0.393 g, 3.8 mmol) and stirred at ambient temperature for16 h. The reaction mixture was then concentrated under reduced pressureand purified by medium pressure liquid chromatography on silica geleluting with 0 to 10% methanol in chloroform to provide 0.570 g of thetitle compound, a compound of the invention, as a solid.

¹H NMR (CDCl₃) δ 16.61 (s, 1H), 8.02 (s, 1H), 7.50 (m, 5H), 3.93 (m,1H), 2.73 (t, 2H), 2.61 (m, 2H), 2.51 (t, 2H), 2.08 (m, 2H), 1.74 (m,4H), 1.51 (d, 1H), 1.19 (m, 1H), 0.97 (m, 2H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 32 can be prepared. Thefollowing abbreviations are used in the Tables which follow: Me meansmethyl, Et means ethyl, n-Pr means normal propyl, i-Pr means isopropyl,c-Pr means cyclopropyl, n-Bu means normal butyl, i-Bu means isobutyl,s-Bu means secondary butyl, c-Bu means cyclobutyl, t-Bu means tertiarybutyl, n-pent means normal pentyl, c-Pent means cyclopentyl, n-Hex meansnormal hexyl, hept means heptyl, c-Hex means cyclohexyl, Ph meansphenyl, OMe means methoxy, OEt means ethoxy, SMe means methylthio, SEtmeans ethylthio, thp means tetrahydropyran, thtp meanstetrahydrothiopyran, thf means tetrahydrofuran, —CN means cyano, —NO₂means nitro, S(O)Me means methylsulfinyl, SO₂ means sulfonyl and S(O)₂Memeans methylsulfonyl.

TABLE 1

R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pent c-Pentn-Hex c-Hex Ph CH₂-c-Pr CH₂-c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph Ph(4-Me)CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂CH₂C≡CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe)CH₂SO₂-n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe)Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe) CH₂Ph(4-OMe) CH₂CH₂SMeCH₂SCH₂Ph CH₂SO₂Ph CH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-Cl)Ph(3,5-di-Cl) Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me)Ph(3,5-di-Me) CH₂-c-Hex Ph(2,3-di-F) Ph(2,4-di-F) Ph(2,5-di-F)Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3 -di-Cl) Ph(3,5-di-F)isoxazolin-2-yl Ph(2-Cl) Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN) Ph(4-CN)Ph(2-F) Ph(3-F) Ph(4-F) CH₂S-n-Pr CH₂-c-Pent oxazolin-2-yl 2-pyridinyl3-pyridinyl 4-pyridinyl Ph(2-NO₂) Ph(3-NO₂) Ph(4-NO₂) Ph(2-CF₃)Ph(3-CF₃) Ph(4-CF₃) Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me)CH₂Ph(4-Me) CH₂Ph(2-Cl) CH₂Ph(3-Cl) CH₂Ph(4-Cl) thiazol-3-ylthiazol-2-yl thiazolin-2-yl thiazol-2-yl oxazol-2-yl CH₂CF₂CF₃ CH═CH₂CH₂(thf-2-yl) CH₂(3-methylisoxazolin-5-yl) isoxazolin-4-ylCH₂(3-methylisoxazol-5-yl) 5-methylisoxazol-3-yl 4-methyloxazol-2-yl4-methylthiazol-2-yl CH₂CH₂CH═CH₂ CH₂SO₂CH₂CH₃ CH₂CH₂SO₂Me CH₂OCH₂OCH₃ 3-methylthiazol-2-yl 5-chloropyridin-2-yl 5-methylpyridin-2-yl5-methoxypyridin-2-yl 6-methylpyridin-2-yl 6-methylpyridin-3-yl3-methoxypyridin-4-yl 3-methylpyridin-4-yl 3-chloropyridin-4-ylCH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ n-hept c-hept thp-4-yl thtp-4-ylPh(2,3-di-OMe) Ph(3,4-di-OMe) Ph(3,4-di-Me) Ph(3,4-di-F)Ph(3,4,5-tri-OMe) Ph(2-I) Ph(3-I) Ph(4-I) Ph(2-Et) Ph(3-Et) Ph(4-Et)CH₂CH₂OCH₂CH₃ CH(CH₃)CH₂OCH₃ Ph(2-OCF₃) Ph(3-OCF₃) Ph(4-OCF₃)Ph(2-Me-3-F) Ph(2-Me-4-F) Ph(2-Me-5-F) Ph(2-F-3-Me) Ph(2-F-4-Me)Ph(2-F-5-Me) Ph(3-F-4-Me) Ph(3-F-5-Me) Ph(3-Me-4-F) CH₂CH₂CH₂OCH₃CH₂CH₂CH₂OCH₂CH₃ CH₂(thp-2-yl) CH₂(thp-4-yl) CH₂CH₂CH═CH₂ CH₂C≡CHCH₂CH₂SCH₃ CH₂CH₂SOCH₃ CH₂CH₂SO₂CH₃ CH₂CH₂CH₂SCH₃ CH₂CH₂CH₂SOCH₃CH₂CH₂CH₂SO₂CH₃ c-hex(3-OCH₃) c-hex(4-OCH₃) c-hex(3,4-di-OCH₃)c-hex(3,5-di-OCH₃) CH₂CH₂SCH₃The present disclosure also includes Tables 1A through 57A, each ofwhich is constructed the same as Table 1 above except that the rowheading in Table 1 (i.e. “R² is Ph”) is replaced with the respective rowheadings shown below. For example, in Table 1A the row heading is “R² isMe”, and R¹ is as defined in Table 1 above. Thus, the first entry inTable 1A specifically discloses a compound of Formula 1 wherein X is CH;Y is C(O); R¹ is Me; R² is Me; R³ is OH; A is A-1; B¹ is C-1; B² is C-3;B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2A through 57Aare constructed similarly.

Table Row Heading  1A R² is Me  2A R² is Et  3A R² is n-Pr  4A R² isc-Pr  5A R² is SMe  6A R² is SO₂Me  7A R² is CF₃  8A R² is Ph(2-Cl)  9AR² is Ph(3-Cl) 10A R² is Ph(4-Cl) 11A R² is Ph(2-Me) 12A R² is Ph(3-Me)13A R² is Ph(4-Me) 14A R² is Ph(2-OMe) 15A R² is Ph(3-OMe) 16A R² isPh(4-OMe) 17A R² is Ph(2-F) 18A R² is Ph(3-F) 19A R² is Ph(4-F) 20A R²is OMe 21A R² is OEt 22A R² is CH₂Ph 23A R² is 2-pyridinyl 24A R² is3-pyridinyl 25A R² is 4-pyridinyl 26A R² is H 27A R² is Ph(3,5-di-F) 28AR² is Ph(3,4-di-F) 29A R² is Ph(3,4,5-tri-F) 30A R² is Ph(2,3-di-F) 31AR² is Ph(3-CF₃) 32A R² is Ph(4-CF₃) 33A R² is Ph(3,5-di-CF₃) 34A R² isn-Bu 35A R² is CH₂OCH₃, 36A R² is CH₂CH₂OCH₃ 37A R² is CH₂CH₂CF₃ 38A R²is CH₂CF₃ 39A R² is n-pent 40A R² is c-pent 41A R² is c-Hex 42A R² isn-Hex 43A R² is thp-4-yl 44A R² is Ph(2-CN) 45A R² is Ph(3-CN) 46A R² isPh(4-CN) 47A R² is Ph(2-C≡CH) 48A R² is Ph(3-C≡CH) 49A R² is Ph(4-C≡CH)50A R² is Ph(3-Me, 2-F) 51A R² is Ph(3-Me-4-F) 52A R² is Ph(3-Me, 5-F)53A R² is Ph(3-Me, 6-F) 54A R² is Ph(3-F, 2-Me) 55A R² is Ph(3-F-4-Me)56A R² is Ph(3-F-5-Me) 57A R² is Ph(3-F, 6-Me)

TABLE 2

R¹ is Me R² R³ R^(14a) R^(15a) R¹⁸ R¹⁹ R^(14b) R^(15b) Et OH Me H H H HH CF₃ OH Me H H H H H n-Pr OH Me H H H H H c-Pr OH Me H H H H H Ph OH MeH H H H H Ph(2-Cl) OH Me H H H H H Ph(3-Cl) OH Me H H H H H Ph(4-Cl) OHMe H H H H H SMe OH Me H H H H H SO₂Me OH Me H H H H H n-Bu OH Me H H HH H Ph(2-F) OH Me H H H H H Ph(3-F) OH Me H H H H H Ph(4-F) OH Me H H HH H Ph(3,5-di-F) OH Me H H H H H Ph(2-Me) OH Me H H H H H Ph(3-Me) OH MeH H H H H Ph(4-Me) OH Me H H H H H Ph(3,5-di-Me) OH Me H H H H H2-pyridinyl OH Me H H H H H 3-pyridinyl OH Me H H H H H 4-pyridinyl OHMe H H H H H Et OH Me Me H H H H CF₃ OH Me Me H H H H n-Pr OH Me Me H HH H c-Pr OH Me Me H H H H Ph OH Me Me H H H H Ph(2-Cl) OH Me Me H H H HPh(3-Cl) OH Me Me H H H H Ph(4-Cl) OH Me Me H H H H SMe OH Me Me H H H HSO₂Me OH Me Me H H H H Et OH H H Me Me H H CF₃ OH H H Me Me H H n-Pr OHH H Me Me H H c-Pr OH H H Me Me H H Ph OH H H Me Me H H Ph(2-Cl) OH H HMe Me H H Ph(3-Cl) OH H H Me Me H H Ph(4-Cl) OH H H Me Me H H SMe OH H HMe Me H H SO₂Me OH H H Me Me H H n-Bu OH H H Me Me H H Ph(2-F) OH H H MeMe H H Ph(3-F) OH H H Me Me H H Ph(4-F) OH H H Me Me H H Ph(3,5-di-F) OHH H Me Me H H Ph(2-Me) OH H H Me Me H H Ph(3-Me) OH H H Me Me H HPh(4-Me) OH H H Me Me H H Ph(3,5-di-Me) OH H H Me Me H H 2-pyridinyl OHH H Me Me H H 3-pyridinyl OH H H Me Me H H 4-pyridinyl OH H H Me Me H HEt OH Me Me H H Me Me CF₃ OH Me Me H H Me Me n-Pr OH Me Me H H Me Mec-Pr OH Me Me H H Me Me Ph OH Me Me H H Me Me Ph(2-Cl) OH Me Me H H MeMe Ph(3-Cl) OH Me Me H H Me Me Ph(4-Cl) OH Me Me H H Me Me SMe OH Me MeH H Me Me SO₂Me OH Me Me H H Me Me n-Bu OH Me Me H H Me Me Ph(2-F) OH MeMe H H Me Me Ph(3-F) OH Me Me H H Me Me Ph(4-F) OH Me Me H H Me MePh(3,5-di-F) OH Me Me H H Me Me Ph(2-Me) OH Me Me H H Me Me Ph(3-Me) OHMe Me H H Me Me Ph(4-Me) OH Me Me H H Me Me Ph(3,5-di-Me) OH Me Me H HMe Me 2-pyridinyl OH Me Me H H Me Me 3-pyridinyl OH Me Me H H Me Me4-pyridinyl OH Me Me H H Me Me Et SPh H H H H H H CF₃ SPh H H H H H Hn-Pr SPh H H H H H H c-Pr SPh H H H H H H Ph SPh H H H H H H Ph(2-Cl)SPh H H H H H H Ph(3-Cl) SPh H H H H H H Ph(4-Cl) SPh H H H H H H SMeSPh H H H H H H SO₂Me SPh H H H H H H n-Bu SPh H H H H H H Ph(2-F) SPh HH H H H H Ph(3-F) SPh H H H H H H Ph(4-F) SPh H H H H H H Ph(3,5-di-F)SPh H H H H H H Ph(2-Me) SPh H H H H H H Ph(3-Me) SPh H H H H H HPh(4-Me) SPh H H H H H H Ph(3,5-di-Me) SPh H H H H H H 2-pyridinyl SPh HH H H H H 3-pyridinyl SPh H H H H H H 4-pyridinyl SPh H H H H H H Et OMeH H H H H H CF₃ OMe H H H H H H n-Pr OMe H H H H H H c-Pr OMe H H H H HH Ph OMe H H H H H H Ph(2-Cl) OMe H H H H H H Ph(3-Cl) OMe H H H H H HPh(4-Cl) OMe H H H H H H SMe OMe H H H H H H SO₂Me OMe H H H H H H n-BuOMe H H H H H H Ph(2-F) OMe H H H H H H Ph(3-F) OMe H H H H H H Ph(4-F)OMe H H H H H H Ph(3,5-di-F) OMe H H H H H H Ph(2-Me) OMe H H H H H HPh(3-Me) OMe H H H H H H Ph(4-Me) OMe H H H H H H Ph(3,5-di-Me) OMe H HH H H H 2-pyridinyl OMe H H H H H H 3-pyridinyl OMe H H H H H H4-pyridinyl OMe H H H H H H Et OSO₂Ph(4-Me) H H H H H H CF₃ OSO₂Ph(4-Me)H H H H H H n-Pr OSO₂Ph(4-Me) H H H H H H c-Pr OSO₂Ph(4-Me) H H H H H HPh OSO₂Ph(4-Me) H H H H H H Ph(2-Cl) OSO₂Ph(4-Me) H H H H H H Ph(3-Cl)OSO₂Ph(4-Me) H H H H H H Ph(4-Cl) OSO₂Ph(4-Me) H H H H H H SMeOSO₂Ph(4-Me) H H H H H H SO₂Me OSO₂Ph(4-Me) H H H H H H n-BuOSO₂Ph(4-Me) H H H H H H Ph(2-F) OSO₂Ph(4-Me) H H H H H H Ph(3-F)OSO₂Ph(4-Me) H H H H H H Ph(4-F) OSO₂Ph(4-Me) H H H H H H Ph(3,5-di-F)OSO₂Ph(4-Me) H H H H H H Ph(2-Me) OSO₂Ph(4-Me) H H H H H H Ph(3-Me)OSO₂Ph(4-Me) H H H H H H Ph(4-Me) OSO₂Ph(4-Me) H H H H H H Ph(3,5-di-Me)OSO₂Ph(4-Me) H H H H H H 2-pyridinyl OSO₂Ph(4-Me) H H H H H H3-pyridinyl OSO₂Ph(4-Me) H H H H H H 4-pyridinyl OSO₂Ph(4-Me) H H H H HH Et OH Me Me —C(O)— Me Me CF₃ OH Me Me —C(O)— Me Me n-Pr OH Me Me—C(O)— Me Me c-Pr OH Me Me —C(O)— Me Me Ph OH Me Me —C(O)— Me MePh(2-Cl) OH Me Me —C(O)— Me Me Ph(3-Cl) OH Me Me —C(O)— Me Me Ph(4-Cl)OH Me Me —C(O)— Me Me SMe OH Me Me —C(O)— Me Me SO₂Me OH Me Me —C(O)— MeMe n-Bu OH Me Me —C(O)— Me Me Ph(2-F) OH Me Me —C(O)— Me Me Ph(3-F) OHMe Me —C(O)— Me Me Ph(4-F) OH Me Me —C(O)— Me Me Ph(3,5-di-F) OH Me Me—C(O)— Me Me Ph(2-Me) OH Me Me —C(O)— Me Me Ph(3-Me) OH Me Me —C(O)— MeMe Ph(4-Me) OH Me Me —C(O)— Me Me Ph(3,5-di-Me) OH Me Me —C(O)— Me Me2-pyridinyl OH Me Me —C(O)— Me Me 3-pyridinyl OH Me M —C(O)— Me Me4-pyridinyl OH Me Me —C(O)— Me MeThe present disclosure also includes Tables 1B through 38B, each ofwhich is constructed the same as Table 2 above except that the rowheading in Table 2 (i.e. “R¹ is Me”) is replaced with the respective rowheadings shown below. For example, in Table 1B the row heading is “R¹ isEt”, and R², R³, R^(14a), R^(15a), R¹⁸, R¹⁹, R^(14b) and R^(15b) are asdefined in Table 2 above. Thus, the first entry in Table 1B specificallydiscloses a compound of Formula 1 wherein X is CH; Y is C(O); R¹ is Et;R² is Et, R³ is OH; A is A-1; B¹ is C-1, B² is C-3 and B³ is C-1;R^(14a) is Me; R^(15a) is H; R¹⁸ is H; is H; R¹⁹ is H; R^(14b) is H; andR^(15b) is H. Tables 2B through 38B are constructed similarly.

Table Row Heading  1B R¹ is Et  2B R¹ is CH₂CF₃  3B R¹ is CH₂CH═CH₂  4BR¹ is CH₂C≡CH  5B R¹ is Ph  6B R¹ is Ph(2-Me)  7B R¹ is Ph(4-Me)  8B R¹is Ph(2-Cl)  9B R¹ is Ph(3-Cl) 10B R¹ is n-Pr 11B R¹ is c-Pr 12B R¹ isn-Bu 13B R¹ is i-Bu 14B R ¹is n-pent 15B R¹ is n-Hex 16B R¹ is thp-4-yl17B R¹ is thtp-4yl 18B R¹ is c-Hex 19B R¹ is CH₂CH₂OCH₃ 20B R¹ isCH₂CH₂OCH₂CH₃ 21B R¹ is CH₂CH₂CH₂OCH₃ 22B R¹ is CH₂CH₂CH₂OCH₂CH₃ 23B R¹is Ph(3-OMe) 24B R¹ is Ph(4-OMe) 25B R¹ is Ph(3,4-di-OMe) 26B R¹ isPh(2-F) 27B R¹ is Ph(3-F) 28B R¹ is Ph(4-F) 29B R¹ is Ph(3-Me) 30B R¹ isPh(2-Me-3-F) 31B R¹ is Ph(2-Me-4-F) 32B R¹ is Ph(2-Me-5-F) 33B R¹ isPh(2-F-3-Me) 34B R¹ is Ph(2-F-4-Me) 35B R¹ is Ph(2-F-5-Me) 36B R¹ isPh(3-F-4-Me) 37B R¹ is Ph(3-F-5-Me) 38B R¹ is Ph(3-Me-4-F)

TABLE 3

R¹ is CH₃, R⁹ CH₃ R² Et n-Pr c-Pr CF₃ SMe Ph Ph(2-Cl) Ph(3-Cl) Ph(4-Cl)Ph(3-F) Ph(3,5-di-F) Ph(3-Me)The present disclosure also includes Tables 1C through 37C, each ofwhich is constructed the same as Table 3 above except that the rowheading in Table 3 (i.e. “R¹ is CH₃, R⁹ is CH₃”) is replaced with therespective row headings shown below. For example, in Table 1C the rowheading is “R¹ is CH₂CH₃, R⁹ is CH₃”, and R² is as defined in Table 3above. Thus, the first entry in Table 1C specifically discloses acompound of Formula 1 wherein X is CH; Y is C(O); R¹ is CH₂CH₃; R² isEt; A is A-5; R³ is OH; R⁹ is CH₃; and R¹⁰ is H. Tables 2C through 27Care constructed similarly.

Table Row Heading  1C R¹ is CH₂CH₃, R⁹ is CH₃  2C R¹ is CH₂CH═CH₂, R⁹ isCH₃  3C R¹ is CH₂C≡CH, R⁹ is CH₃  4C R¹ is Ph, R⁹ is CH₃  5C R¹ isPh(2-Me), R⁹ is CH₃  6C R¹ is Ph(4-Me), R⁹ is CH₃  7C R¹ is Ph(2-Me), R⁹is CH₃  8C R¹ is Ph(3-Cl), R⁹ is CH₃  9C R¹ is CH₃, R⁹ is CH₂CH₃ 10C R¹is CH₂CH₃, R⁹ is CH₂CH₃ 11C R¹ is CH₂CH═CH₂, R⁹ is CH₂CH₃ 12C R¹ isCH₂C≡CH, R⁹ is CH₂CH₃ 13C R¹ is Ph, R⁹ is CH₂CH₃ 14C R¹ is Ph(2-Me), R⁹is CH₂CH₃ 15C R¹ is Ph(4-Me), R⁹ is CH₂CH₃ 16C R¹ is Ph(2-Cl), R⁹ isCH₂CH₃ 17C R¹ is Ph(3-Cl), R⁹ is CH₂CH₃ 18C R¹ is n-Bu, R⁹ is CH₃ 19C R¹is n-pent, R⁹ is CH₃ 20C R¹ is n-Hex, R⁹ is CH₃ 21C R¹ is thp-4-yl, R⁹is CH₃ 22C R¹ is thtp-4-yl, R⁹ is CH₃ 23C R¹ is c-Hex, R⁹ is CH₃ 24C R¹is CH₂CH₂OCH₃, R⁹ is CH₃ 25C R¹ is CH₂CH₂OCH₂CH₃, R⁹ is CH₃ 26C R¹ isCH₂CH₂CH₂OCH₃, R⁹ is CH₃ 27C R¹ is CH₂CH₂CH₂OEt, R⁹ is CH₃ 28C R¹ isn-Bu, R⁹ is CH₂CH₃ 29C R¹ is n-pent, R⁹ is CH₂CH₃ 30C R¹ is n-Hex, R⁹ isCH₂CH₃ 31C R¹ is thp-4-yl, R⁹ is CH₂CH₃ 32C R¹ is thtp-4-yl, R⁹ isCH₂CH₃ 33C R¹ is c-Hex, R⁹ is CH₂CH₃ 34C R¹ is CH₂CH₂OCH₃, R⁹ is CH₂CH₃35C R¹ is CH₂CH₂OCH₂CH₃, R⁹ is CH₂CH₃ 36C R¹ is CH₂CH₂CH₂OCH₃, R⁹ isCH₂CH₃ 37C R¹ is CH₂CH₂CH₂OEt, R⁹ is CH₂CH₃

TABLE 4

R¹ is CH₃, R⁹ is CH₃ R² Et n-Pr c-Pr CF₃ SMe Ph Ph(2-Cl) Ph(3-Cl)Ph(4-Cl) Ph(3-F) Ph(3,5-di-F) Ph(3-Me)The present disclosure also includes Tables 1D through 37D, each ofwhich is constructed the same as Table 4 above except that the rowheading in Table 4 (i.e. “R¹ is CH₃, R⁹ is CH₃”) is replaced with therespective row headings shown below. For example, in Table 1D the rowheading is “R¹ is CH₂CH₃, R⁹ is CH₃”, and R² is as defined in Table 4above. Thus, the first entry in Table 1D specifically discloses acompound of Formula 1 wherein X is CH; Y is C(O); R¹ is CH₂CH₃; R² isEt; A is A-5; R³ is OH; R⁹ is CH₃; and R¹⁰ is CH₃. Tables 2D through 37Dare constructed similarly.

Table Row Heading  1D R¹ is CH₂CH₃, R⁹ is CH₃  2D R¹ is CH₂CH═CH₂, R⁹ isCH₃  3D R¹ is CH₂C≡CH, R⁹ is CH₃  4D R¹ is Ph, R⁹ is CH₃  5D R¹ isPh(2-Me), R⁹ is CH₃  6D R¹ is Ph(4-Me), R⁹ is CH₃  7D R¹ is Ph(2-Me), R⁹is CH₃ R⁵ is CH₃  8D R¹ is Ph(3-Cl), R⁹ is CH₃  9D R¹ is CH₃, R⁹ isCH₂CH₃ 10D R¹ is CH₂CH₃, R⁹ is CH₂CH₃ 11D R¹ is CH₂CH═CH₂, R⁹ is CH₂CH₃12D R¹ is CH₂C≡CH, R⁹ is CH₂CH₃ 13D R¹ is Ph, R⁹ is CH₂CH₃ 14D R¹ isPh(2-Me), R⁹ is CH₂CH₃ 15D R¹ is Ph(4-Me), R⁹ is CH₂CH₃ 16D R¹ isPh(2-Cl), R⁹ is CH₂CH₃ 17D R¹ is Ph(3-Cl), R⁹ is CH₂CH₃ 18D R¹ is n-Bu,R⁹ is CH₃ 19D R¹ is n-pent, R⁹ is CH₃ 20D R¹ is n-Hex, R⁹ is CH₃ 21D R¹is thp-4-yl, R⁹ is CH₃ 22D R¹ is thtp-4-yl, R⁹ is CH₃ 23D R¹ is c-Hex,R⁹ is CH₃ 24D R¹ is CH₂CH₂OCH₃, R⁹ is CH₃ 25D R¹ is CH₂CH₂OCH₂CH₃, R⁹ isCH₃ 26D R¹ is CH₂CH₂CH₂OCH₃, R⁹ is CH₃ 27D R¹ is CH₂CH₂CH₂OEt, R⁹ is CH₃28D R¹ is n-Bu, R⁹ is CH₂CH₃ 29D R¹ is n-pent, R⁹ is CH₂CH₃ 30D R¹ isn-Hex, R⁹ is CH₂CH₃ 31D R¹ is thp-4-yl, R⁹ is CH₂CH₃ 32D R¹ isthtp-4-yl, R⁹ is CH₂CH₃ 33D R¹ is c-Hex, R⁹ is CH₂CH₃ 34D R¹ isCH₂CH₂OCH₃, R⁹ is CH₂CH₃ 35D R¹ is CH₂CH₂OCH₂CH₃, R⁹ is CH₂CH₃ 36D R¹ isCH₂CH₂CH₂OCH₃, R⁹ is CH₂CH₃ 37D R¹ is CH₂CH₂CH₂OEt, R⁹ is CH₂CH₃

TABLE 5

R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pent c-Pentn-Hex c-Hex Ph CH₂-c-Pr CH₂-c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph Ph(4-Me)CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂CH₂C≡CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe)CH₂SO₂-n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe)Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe) CH₂Ph(4-OMe) CH₂CH₂SMeCH₂SCH₂Ph CH₂SO₂Ph CH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-Cl)Ph(3,5-di-Cl) Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me)Ph(3,5-di-Me) CH₂-c-Hex Ph(2,3-di-F) Ph(2,4-di-F) Ph(2,5-di-F)Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl) Ph(3,5-di-F)isoxazolin-2-yl Ph(2-Cl) Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN) Ph(4-CN)Ph(2-F) Ph(3-F) Ph(4-F) CH₂S-n-Pr CH₂-c-Pent oxazolin-2-yl 2-pyridinyl3-pyridinyl 4-pyridinyl Ph(2-NO₂) Ph(3-NO₂) Ph(4-NO₂) Ph(2-CF₃)Ph(3-CF₃) Ph(4-CF₃) Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me)CH₂Ph(4-Me) CH₂Ph(2-Cl) CH₂Ph(3-Cl) CH₂Ph(4-Cl) thiazol-3-ylthiazol-2-yl thiazolin-2-yl thiazol-2-yl oxazol-2-yl CH₂CF₂CF₃ CH═CH₂CH₂(thf-2-yl) CH₂(3-methylisoxazolin-5-yl) isoxazolin-4-ylCH₂(3-methylisoxazol-5-yl) 5-methylisoxazol-3-yl 4-methyloxazol-2-yl4-methylthiazol-2-yl CH₂CH₂CH═CH₂ CH₂SO₂CH₂CH₃ CH₂CH₂SO₂Me CH₂OCH₂OCH₃3-methylthiazol-2-yl 5-chloropyridin-2-yl 5-methylpyridin-2-yl5-methoxypyridin-2-yl 6-methylpyridin-2-yl 6-methylpyridin-3-yl3-methoxypyridin-4-yl 3-methylpyridin-4-yl 3-chloropyridin-4-ylCH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ n-hept c-hept thp-4-yl thtp-4-ylPh(2,3-di-OMe) Ph(3,4-di-OMe) Ph(3,4-di-Me) Ph(3,4-di-F)Ph(3,4,5-tri-OMe) Ph(2-I) Ph(3-I) Ph(4-I) Ph(2-Et) Ph(3-Et) Ph(4-Et)CH₂CH₂OCH₂CH₃ CH(CH₃)CH₂OCH₃ Ph(2-OCF₃) Ph(3-OCF₃) Ph(4-OCF₃)Ph(2-Me-3-F) Ph(2-Me-4-F) Ph(2-Me-5-F) Ph(2-F-3-Me) Ph(2-F-4-Me)Ph(2-F-5-Me) Ph(3-F-4-Me) Ph(3-F-5-Me) Ph(3-Me-4-F) CH₂CH₂CH₂OCH₃CH₂CH₂CH₂OCH₂CH₃ CH₂(thp-2-yl) CH₂(thp-4-yl) CH₂CH₂CH═CH₂ CH₂C≡CHCH₂CH₂SCH₃ CH₂CH₂SOCH₃ CH₂CH₂SO₂CH₃ CH₂CH₂CH₂SCH₃ CH₂CH₂CH₂SOCH₃CH₂CH₂CH₂SO₂CH₃ c-hex(3-OCH₃) c-hex(4-OCH₃) c-hex(3,4-di-OCH₃)c-hex(3,5-di-OCH₃) CH₂CH₂SCH₃The present disclosure also includes Tables 1E through 57E, each ofwhich is constructed the same as Table 1 above except that the rowheading in Table 1 (i.e. “R² is Ph”) is replaced with the respective rowheadings shown below. For example, in Table 1E the row heading is “R² isMe”, and R¹ is as defined in Table 5 above. Thus, the first entry inTable 1E specifically discloses a compound of Formula 1 wherein X is CH;Y is C(O); R¹ is Me; R² is Me; R³ is OH; A is A-1; B¹ is C-1; B² is C-3;B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2E through 57Eare constructed similarly.

Table Row Heading  1E R² is Me  2E R² is Et  3E R² is n-Pr  4E R² isc-Pr  5E R² is SMe  6E R² is SO₂Me  7E R² is CF₃  8E R² is Ph(2-Cl)  9ER² is Ph(3-Cl) 10E R² is Ph(4-Cl) 11E R² is Ph(2-Me) 12E R² is Ph(3-Me)13E R² is Ph(4-Me) 14E R² is Ph(2-OMe) 15E R² is Ph(3-OMe) 16E R² isPh(4-OMe) 17E R² is Ph(2-F) 18E R² is Ph(3-F) 19E R² is Ph(4-F) 20E R²is OMe 21E R² is OEt 22E R² is CH₂Ph 23E R² is 2-pyridinyl 24E R² is3-pyridinyl 25E R² is 4-pyridinyl 26E R² is H 27E R² is Ph(3,5-di-F) 28ER² is Ph(3,4-di-F) 29E R² is Ph(3,4,5-tri-F) 30E R² is Ph(2,3-di-F) 31ER² is Ph(3-CF₃) 32E R² is Ph(4-CF₃) 33E R² is Ph(3,5-di-CF₃) 34E R² isn-Bu 35E R² is CH₂OCH₃ 36E R² is CH₂CH₂OCH₃ 37E R² is CH₂CH₂CF₃ 38E R²is CH₂CF₃ 39E R² is n-pent 40E R² is c-pent 41E R² is c-Hex 42E R² isn-Hex 43E R² is thp-4-yl 44E R² is Ph(2-CN) 45E R² is Ph(3-CN) 46E R² isPh(4-CN) 47E R² is Ph(2-C≡CH) 48E R² is Ph(3-C≡CH) 49E R² is Ph(4-C≡CH)50E R² is Ph(3-Me, 2-F) 51E R² is Ph(3-Me-4-F) 52E R² is Ph(3-Me, 5-F)53E R² is Ph(3-Me, 6-F) 54E R² is Ph(3-F, 2-Me) 55E R² is Ph(3-F-4-Me)56E R² is Ph(3-F-5-Me) 57E R² is Ph(3-F, 6-Me)

TABLE 6

R¹ is phenyl R² R³ Et OMe n-Pr OMe c-Pr OMe CF₃ OMe SMe OMe Ph OMePh(3-F) OMe Ph(3,5-di-F) OMe Ph(3-Me) OMe Et SPh n-Pr SPh c-Pr SPh CF₃SPh SMe SPh Ph SPh Ph(3-F) SPh Ph(3,5-di-F) SPh Ph(3-Me) SPh Et OSO₂Phn-Pr OSO₂Ph c-Pr OSO₂Ph CF₃ OSO₂Ph SMe OSO₂Ph Ph OSO₂Ph Ph(3-F) OSO₂PhPh(3,5-di-F) OSO₂Ph Ph(3-Me) OSO₂Ph Et OC(O)Ph n-Pr OC(O)Ph c-Pr OC(O)PhCF₃ OC(O)Ph SMe OC(O)Ph Ph OC(O)Ph Et OC(O)Ph Ph(3-F) OC(O)PhPh(3,5-di-F) OC(O)Ph Ph(3-Me) OC(O)Ph n-Pr OC(O)CH₃ c-Pr OC(O)CH₃ CF₃OC(O)CH₃ SMe OC(O)CH₃ Ph OC(O)CH₃ Ph(3-F) OC(O)CH₃ Ph(3,5-di-F) OC(O)CH₃Ph(3-Me) OC(O)CH₃The present disclosure also includes Tables 1F through 11F, each ofwhich is constructed the same as Table 6 above except that the rowheading in Table 6 (i.e. “R¹ is Ph”) is replaced with the respective rowheadings shown below. For example, in Table 1F the row heading is “R¹ isn-Pr”, and R² is as defined in Table 6 above. Thus, the first entry inTable 1F specifically discloses a compound of Formula 1 wherein X is CH;Y is C(O); R¹ is phenyl; R² n-Pr; R³ is OMe; A is A-3; B² is C-3; T is—CH₂CH₂—; R¹⁸ and R¹⁹ are both H. Tables 2F through 11F are constructedsimilarly.

Table Row Heading 1F R¹ is n-Pr 2F R¹ is n-Bu 3F R¹ is n-pent 4F R¹ isn-Hex 5F R¹ is thp-4-yl 6F R¹ is thtp-4-yl 7F R¹ is c-Hex 8F R¹ isCH₂CH₂OCH₃ 9F R¹ is CH₂CH₂OCH₂CH₃ 10F  R¹ is CH₂CH₂CH₂OCH₃ 11F  R¹ isCH₂CH₂CH₂OCH₂CH₃

TABLE 7

R² R² R² R² R² R² Et n-Pr c-Pr CF₃ SMe Ph Ph(2-Me) Ph(3-Cl) Ph(4-Cl)Ph(2-Me) Ph(3-Me) Ph(4-Me)

TABLE 8

R¹² is c-Pr R¹ R² CH₃ Et CH₃ n-Pr CH₃ c-Pr CH₃ CF₃ CH₃ SMe CH₃ Ph CH₃Ph(2-Cl) CH₃ Ph(3-Cl) CH₃ Ph(4-Cl) CH₃ Ph(3-F) CH₃ Ph(3,5-di-F) CH₃Ph(3-Me) Et Et Et n-Pr Et c-Pr Et CF₃ Et SMe Et Ph Et Ph(2-Cl) EtPh(3-Cl) Et Ph(4-Cl) Et Ph(3-F) Et Ph(3,5-di-F) Et Ph(3-Me) CH₂CH═CH₂ EtCH₂CH═CH₂ n-Pr CH₂CH═CH₂ c-Pr CH₂CH═CH₂ CF₃ CH₂CH═CH₂ SMe CH₂CH═CH₂ PhCH₂CH═CH₂ Ph(2-Cl) CH₂CH═CH₂ Ph(3-Cl) CH₂CH═CH₂ Ph(4-Cl) CH₂CH═CH₂Ph(3-F) CH₂CH═CH₂ Ph(3,5-di-F) CH₂CH═CH₂ Ph(3-Me) CH₂C≡CH Et CH₂C≡CHn-Pr CH₂C≡CH c-Pr CH₂C≡CH CF₃ CH₂C≡CH SMe CH₂C≡CH Ph CH₂C≡CH Ph(2-Cl)CH₂C≡CH Ph(3-Cl) CH₂C≡CH Ph(4-Cl) CH₂C≡CH Ph(3-F) CH₂C≡CH Ph(3,5-di-F)CH₂C≡CH Ph(3-Me) Ph Et Ph n-Pr Ph c-Pr Ph CF₃ Ph SMe Ph Ph Ph Ph(2-Cl)Ph Ph(3-Cl) Ph Ph(4-Cl) Ph Ph(3-F) Ph Ph(3,5-di-F) Ph Ph(3-Me) Ph(2-Me)Et Ph(2-Me) n-Pr Ph(2-Me) c-Pr Ph(2-Me) CF₃ Ph(2-Me) SMe Ph(2-Me) PhPh(2-Me) Ph(2-Cl) Ph(2-Me) Ph(3-Cl) Ph(2-Me) Ph(4-Cl) Ph(2-Me) Ph(3-F)Ph(2-Me) Ph(3,5-di-F) Ph(2-Me) Ph(3-Me) Ph(4-Me) Et Ph(4-Me) n-PrPh(4-Me) c-Pr Ph(4-Me) CF₃ Ph(4-Me) SMe Ph(4-Me) Ph Ph(4-Me) Ph(2-Cl)Ph(4-Me) Ph(3-Cl) Ph(4-Me) Ph(4-Cl) Ph(4-Me) Ph(3-F) Ph(4-Me)Ph(3,5-di-F) Ph(4-Me) Ph(3-Me) Ph(2-Cl) Et Ph(2-Cl) n-Pr Ph(2-Cl) c-PrPh(2-Cl) CF₃ Ph(2-Cl) SMe Ph(2-Cl) Ph Ph(2-Cl) Ph(2-Cl) Ph(2-Cl)Ph(3-Cl) Ph(2-Cl) Ph(4-Cl) Ph(2-Cl) Ph(3-F) Ph(2-Cl) Ph(3,5-di-F)Ph(2-Cl) Ph(3-Me) Ph(3-Cl) Et Ph(3-Cl) n-Pr Ph(3-Cl) c-Pr Ph(3-Cl) CF₃Ph(3-Cl) SMe Ph(3-Cl) Ph Ph(3-Cl) Ph(2-Cl) Ph(3-Cl) Ph(3-Cl) Ph(3-Cl)Ph(4-Cl) Ph(3-Cl) Ph(3-F) Ph(3-Cl) Ph(3,5-di-F) Ph(3-Cl) Ph(3-Me) n-PrEt n-Pr n-Pr n-Pr c-Pr n-Pr CF₃ n-Pr SMe n-Pr Ph n-Pr Ph(2-Cl) n-PrPh(3-Cl) n-Pr Ph(4-Cl) n-Pr Ph(3-F) n-Pr Ph(3,5-di-F) n-Pr Ph(3-Me) c-PrEt c-Pr n-Pr c-Pr c-Pr c-Pr CF₃ c-Pr SMe c-Pr Ph c-Pr Ph(2-Cl) c-PrPh(3-Cl) c-Pr Ph(4-Cl) c-Pr Ph(3-F) c-Pr Ph(3,5-di-F) c-Pr Ph(3-Me) n-BuEt n-Bu n-Pr n-Bu c-Pr n-Bu CF₃ n-Bu SMe n-Bu Ph n-Bu Ph(2-Cl) n-BuPh(3-Cl) n-Bu Ph(4-Cl) n-Bu Ph(3-F) n-Bu Ph(3,5-di-F) n-Bu Ph(3-Me)n-pent Et n-pent n-Pr n-pent c-Pr n-pent CF₃ n-pent SMe n-pent Ph n-pentPh(2-Cl) n-pent Ph(3-Cl) n-pent Ph(4-Cl) n-pent Ph(3-F) n-pentPh(3,5-di-F) n-pent Ph(3-Me) n-Hex Et n-Hex n-Pr n-Hex c-Pr n-Hex CF₃n-Hex SMe n-Hex Ph n-Hex Ph(2-Cl) n-Hex Ph(3-Cl) n-Hex Ph(4-Cl) n-HexPh(3-F) n-Hex Ph(3,5-di-F) n-Hex Ph(3-Me) thp-4-yl Et thp-4-yl n-Prthp-4-yl c-Pr thp-4-yl CF₃ thp-4-yl SMe thp-4-yl Ph thp-4-yl Ph(2-Cl)thp-4-yl Ph(3-Cl) thp-4-yl Ph(4-Cl) thp-4-yl Ph(3-F) thp-4-ylPh(3,5-di-F) thp-4-yl Ph(3-Me) c-Hex Et c-Hex n-Pr c-Hex c-Pr c-Hex CF₃c-Hex SMe c-Hex Ph c-Hex Ph(2-Cl) c-Hex Ph(3-Cl) c-Hex Ph(4-Cl) c-HexPh(3-F) c-Hex Ph(3,5-di-F) c-Hex Ph(3-Me) CH₂CH₂OCH₃ Et CH₂CH₂OCH₃ n-PrCH₂CH₂OCH₃ c-Pr CH₂CH₂OCH₃ CF₃ CH₂CH₂OCH₃ SMe CH₂CH₂OCH₃ Ph CH₂CH₂OCH₃Ph(2-Cl) CH₂CH₂OCH₃ Ph(3-Cl) CH₂CH₂OCH₃ Ph(4-Cl) CH₂CH₂OCH₃ Ph(3-F)CH₂CH₂OCH₃ Ph(3,5-di-F) CH₂CH₂OCH₃ Ph(3-Me) CH₂CH₂OCH₂CH₃ EtCH₂CH₂OCH₂CH₃ n-Pr CH₂CH₂OCH₂CH₃ c-Pr CH₂CH₂OCH₂CH₃ CF₃ CH₂CH₂OCH₂CH₃SMe CH₂CH₂OCH₂CH₃ Ph CH₂CH₂OCH₂CH₃ Ph(2-Cl) CH₂CH₂OCH₂CH₃ Ph(3-Cl)CH₂CH₂OCH₂CH₃ Ph(4-Cl) CH₂CH₂OCH₂CH₃ Ph(3-F) CH₂CH₂OCH₂CH₃ Ph(3,5-di-F)CH₂CH₂OCH₂CH₃ Ph(3-Me) CH₂CH₂CH₂OCH₃ Et CH₂CH₂CH₂OCH₃ n-Pr CH₂CH₂CH₂OCH₃c-Pr CH₂CH₂CH₂OCH₃ CF₃ CH₂CH₂CH₂OCH₃ SMe CH₂CH₂CH₂OCH₃ Ph CH₂CH₂CH₂OCH₃Ph(2-Cl) CH₂CH₂CH₂OCH₃ Ph(3-Cl) CH₂CH₂CH₂OCH₃ Ph(4-Cl) CH₂CH₂CH₂OCH₃Ph(3-F) CH₂CH₂CH₂OCH₃ Ph(3,5-di-F) CH₂CH₂CH₂OCH₃ Ph(3-Me) CH₂CH₂CH₂OEtEt CH₂CH₂CH₂OEt n-Pr CH₂CH₂CH₂OEt c-Pr CH₂CH₂CH₂OEt CF₃ CH₂CH₂CH₂OEt SMeCH₂CH₂CH₂OEt Ph CH₂CH₂CH₂OEt Ph(2-Cl) CH₂CH₂CH₂OEt Ph(3-Cl) CH₂CH₂CH₂OEtPh(4-Cl) CH₂CH₂CH₂OEt Ph(3-F) CH₂CH₂CH₂OEt Ph(3,5-di-F) CH₂CH₂CH₂OEtPh(3-Me)The present disclosure also includes Tables 1H through 2H, each of whichis constructed the same as Table 8 above except that the row heading inTable 8 (i.e. “R¹² is c-Pr”) is replaced with the respective rowheadings shown below. For example, in Table 1H the row heading is “R¹²is CH₃”, and R¹ and R² are as defined in Table 8 above. Thus, the firstentry in Table 1H specifically discloses a compound of Formula 1 whereinX is CH; Y is C(O); R¹ is CH₃; R² is Et; A is A-6; R¹¹ is H; and R¹² isCH₃. Table 2H is constructed similarly.

Table Row Heading 1H R¹² is CH₃ 2H R¹² is CH₂CH₃

TABLE 9

R¹² is c-Pr R¹ R² CH₃ Et CH₃ n-Pr CH₃ c-Pr CH₃ CF₃ CH₃ SMe CH₃ Ph CH₃Ph(2-Cl) CH₃ Ph(3-Cl) CH₃ Ph(4-Cl) CH₃ Ph(3-F) CH₃ Ph(3,5-di-F) CH₃Ph(3-Me) Et Et Et n-Pr Et c-Pr Et CF₃ Et SMe Et Ph Et Ph(2-Cl) EtPh(3-Cl) Et Ph(4-Cl) Et Ph(3-F) Et Ph(3,5-di-F) Et Ph(3-Me) CH₂CH═CH₂ EtCH₂CH═CH₂ n-Pr CH₂CH═CH₂ c-Pr CH₂CH═CH₂ CF₃ CH₂CH═CH₂ SMe CH₂CH═CH₂ PhCH₂CH═CH₂ Ph(2-Cl) CH₂CH═CH₂ Ph(3-Cl) CH₂CH═CH₂ Ph(4-Cl) CH₂CH═CH₂Ph(3-F) CH₂CH═CH₂ Ph(3,5-di-F) CH₂CH═CH₂ Ph(3-Me) CH₂C≡CH Et CH₂C≡CHn-Pr CH₂C≡CH c-Pr CH₂C≡CH CF₃ CH₂C≡CH SMe CH₂C≡CH Ph CH₂C≡CH Ph(2-Cl)CH₂C≡CH Ph(3-Cl) CH₂C≡CH Ph(4-Cl) CH₂C≡CH Ph(3-F) CH₂C≡CH Ph(3,5-di-F)CH₂C≡CH Ph(3-Me) Ph Et Ph n-Pr Ph c-Pr Ph CF₃ Ph SMe Ph Ph Ph Ph(2-Cl)Ph Ph(3-Cl) Ph Ph(4-Cl) Ph Ph(3-F) Ph Ph(3,5-di-F) Ph Ph(3-Me) Ph(2-Me)Et Ph(2-Me) n-Pr Ph(2-Me) c-Pr Ph(2-Me) CF₃ Ph(2-Me) SMe Ph(2-Me) PhPh(2-Me) Ph(2-Cl) Ph(2-Me) Ph(3-Cl) Ph(2-Me) Ph(4-Cl) Ph(2-Me) Ph(3-F)Ph(2-Me) Ph(3,5-di-F) Ph(2-Me) Ph(3-Me) Ph(4-Me) Et Ph(4-Me) n-PrPh(4-Me) c-Pr Ph(4-Me) CF₃ Ph(4-Me) SMe Ph(4-Me) Ph Ph(4-Me) Ph(2-Cl)Ph(4-Me) Ph(3-Cl) Ph(4-Me) Ph(4-Cl) Ph(4-Me) Ph(3-F) Ph(4-Me)Ph(3,5-di-F) Ph(4-Me) Ph(3-Me) Ph(2-Cl) Et Ph(2-Cl) n-Pr Ph(2-Cl) c-PrPh(2-Cl) CF₃ Ph(2-Cl) SMe Ph(2-Cl) Ph Ph(2-Cl) Ph(2-Cl) Ph(2-Cl)Ph(3-Cl) Ph(2-Cl) Ph(4-Cl) Ph(2-Cl) Ph(3-F) Ph(2-Cl) Ph(3,5-di-F)Ph(2-Cl) Ph(3-Me) Ph(3-Cl) Et Ph(3-Cl) n-Pr Ph(3-Cl) c-Pr Ph(3-Cl) CF₃Ph(3-Cl) SMe Ph(3-Cl) Ph Ph(3-Cl) Ph(2-Cl) Ph(3-Cl) Ph(3-Cl) Ph(3-Cl)Ph(4-Cl) Ph(3-Cl) Ph(3-F) Ph(3-Cl) Ph(3,5-di-F) Ph(3-Cl) Ph(3-Me) n-PrEt n-Pr n-Pr n-Pr c-Pr n-Pr CF₃ n-Pr SMe n-Pr Ph n-Pr Ph(2-Cl) n-PrPh(3-Cl) n-Pr Ph(4-Cl) n-Pr Ph(3-F) n-Pr Ph(3,5-di-F) n-Pr Ph(3-Me) n-BuEt n-Bu n-Pr n-Bu c-Pr n-Bu CF₃ n-Bu SMe n-Bu Ph n-Bu Ph(2-Cl) n-BuPh(3-Cl) n-Bu Ph(4-Cl) n-Bu Ph(3-F) n-Bu Ph(3,5-di-F) n-Bu Ph(3-Me)n-pent Et n-pent n-Pr n-pent c-Pr n-pent CF₃ n-pent SMe n-pent Ph n-pentPh(2-Cl) n-pent Ph(3-Cl) n-pent Ph(4-Cl) n-pent Ph(3-F) n-pentPh(3,5-di-F) n-pent Ph(3-Me) n-Hex Et n-Hex n-Pr n-Hex c-Pr n-Hex CF₃n-Hex SMe n-Hex Ph n-Hex Ph(2-Cl) n-Hex Ph(3-Cl) n-Hex Ph(4-Cl) n-HexPh(3-F) n-Hex Ph(3,5-di-F) n-Hex Ph(3-Me) thp-4-yl Et thp-4-yl n-Prthp-4-yl c-Pr thp-4-yl CF₃ thp-4-yl SMe thp-4-yl Ph thp-4-yl Ph(2-Cl)thp-4-yl Ph(3-Cl) thp-4-yl Ph(4-Cl) thp-4-yl Ph(3-F) thp-4-ylPh(3,5-di-F) thp-4-yl Ph(3-Me) thtp-4-yl Et thtp-4-yl n-Pr thtp-4-ylc-Pr thtp-4-yl CF₃ thtp-4-yl SMe thtp-4-yl Ph thtp-4-yl Ph(2-Cl)thtp-4-yl Ph(3-Cl) thtp-4-yl Ph(4-Cl) thtp-4-yl Ph(3-F) thtp-4-ylPh(3,5-di-F) thtp-4-yl Ph(3-Me) c-Hex Et c-Hex n-Pr c-Hex c-Pr c-Hex CF₃c-Hex SMe c-Hex Ph c-Hex Ph(2-Cl) c-Hex Ph(3-Cl) c-Hex Ph(4-Cl) c-HexPh(3-F) c-Hex Ph(3,5-di-F) c-Hex Ph(3-Me) CH₂CH₂OCH₃ Et CH₂CH₂OCH₃ n-PrCH₂CH₂OCH₃ c-Pr CH₂CH₂OCH₃ CF₃ CH₂CH₂OCH₃ SMe CH₂CH₂OCH₃ Ph CH₂CH₂OCH₃Ph(2-Cl) CH₂CH₂OCH₃ Ph(3-Cl) CH₂CH₂OCH₃ Ph(4-Cl) CH₂CH₂OCH₃ Ph(3-F)CH₂CH₂OCH₃ Ph(3,5-di-F) CH₂CH₂OCH₃ Ph(3-Me) CH₂CH₂OCH₂CH₃ EtCH₂CH₂OCH₂CH₃ n-Pr CH₂CH₂OCH₂CH₃ c-Pr CH₂CH₂OCH₂CH₃ CF₃ CH₂CH₂OCH₂CH₃SMe CH₂CH₂OCH₂CH₃ Ph CH₂CH₂OCH₂CH₃ Ph(2-Cl) CH₂CH₂OCH₂CH₃ Ph(3-Cl)CH₂CH₂OCH₂CH₃ Ph(4-Cl) CH₂CH₂OCH₂CH₃ Ph(3-F) CH₂CH₂OCH₂CH₃ Ph(3,5-di-F)CH₂CH₂OCH₂CH₃ Ph(3-Me) CH₂CH₂CH₂OCH₃ Et CH₂CH₂CH₂OCH₃ n-Pr CH₂CH₂CH₂OCH₃c-Pr CH₂CH₂CH₂OCH₃ CF₃ CH₂CH₂CH₂OCH₃ SMe CH₂CH₂CH₂OCH₃ Ph CH₂CH₂CH₂OCH₃Ph(2-Cl) CH₂CH₂CH₂OCH₃ Ph(3-Cl) CH₂CH₂CH₂OCH₃ Ph(4-Cl) CH₂CH₂CH₂OCH₃Ph(3-F) CH₂CH₂CH₂OCH₃ Ph(3,5-di-F) CH₂CH₂CH₂OCH₃ Ph(3-Me) CH₂CH₂CH₂OEtEt CH₂CH₂CH₂OEt n-Pr CH₂CH₂CH₂OEt c-Pr CH₂CH₂CH₂OEt CF₃ CH₂CH₂CH₂OEt SMeCH₂CH₂CH₂OEt Ph CH₂CH₂CH₂OEt Ph(2-Cl) CH₂CH₂CH₂OEt Ph(3-Cl) CH₂CH₂CH₂OEtPh(4-Cl) CH₂CH₂CH₂OEt Ph(3-F) CH₂CH₂CH₂OEt Ph(3,5-di-F) CH₂CH₂CH₂OEtPh(3-Me)The present disclosure also includes Tables 1J through 2J, each of whichis constructed the same as Table 9 above except that the row heading inTable 9 (i.e. “R¹² is c-Pr”) is replaced with the respective rowheadings shown below. For example, in Table 1J the row heading is “R¹²is CH₃”, and R¹ and R² are as defined in Table 9 above. Thus, the firstentry in Table 1J specifically discloses a compound of Formula 1 whereinX is CH; Y is C(O); R¹ is CH₃; R² is Et; A is A-7; R¹² is CH₃; and R¹³is cyano. Table 2J is constructed similarly.

Table Row Heading IJ R¹² is CH₃ 2J R¹² is CH₂CH₃

TABLE 10

R¹ is phenyl R² Et Ph(2-Me) n-Pr Ph(3-Cl) c-Pr Ph(4-Cl) CF₃ Ph(2-Me) SMePh(3-Me) Ph Ph(4-Me) Ph(3-F) Ph(3,5-di-F) Ph(3-Me)The present disclosure also includes Tables 1K through 10K, each ofwhich is constructed the same as Table 9 above except that the rowheading in Table 10 (i.e. “R¹ is Ph”) is replaced with the respectiverow headings shown below. For example, in Table 1K the row heading is“R¹ is n-Bu”, and R² is as defined in Table 10 above. Thus, the firstentry in Table 1K specifically discloses a compound of Formula 1 whereinX is CH; Y is C(O); R¹ is n-Bu; R² is Ph; A is A-7; R¹² is hydroxy; andR¹³ is nitro. Table 2K through 10K are constructed similarly.

Table Row Heading 1K R¹ is n-Bu 2K R¹ is n-pent 3K R¹ is n-Hex 4K R¹ isthp-4-yl 5K R¹ is thtp-4-yl 6K R¹ is c-Hex 7K R¹ is CH₂CH₂OCH₃ 8K R¹ isCH₂CH₂OCH₂CH₃ 9K R¹ is CH₂CH₂CH₂OCH₃ 10K  R¹ is CH₂CH₂CH₂OCH₂CH₃

TABLE 11

R²⁴ R²⁴ R²⁴ R²⁴ R²⁴ Q is CH₂ H Et n-Pr OCH₂CH₂OCH₃ Ph(4-OMe) Ph Ph(3-Cl)Ph(3-F) Ph(3-OMe) Ph(3,5-di-F) Q is —CH₂CH₂— H Et n-Pr OCH₂CH₂OCH₃Ph(4-OMe) Ph Ph(3-Cl) Ph(3-F) Ph(3-OMe) Ph(3,5-di-F) Q is O H Et n-PrOCH₂CH₂OCH₃ Ph(4-OMe) Ph Ph(3-Cl) Ph(3-F) Ph(3-OMe) Ph(3,5-di-F) Q isNCH₃ H Et n-Pr OCH₂CH₂OCH₃ Ph(4-OMe) Ph Ph(3-Cl) Ph(3-F) Ph(3-OMe)Ph(3,5-di-F) Q is S H Et n-Pr OCH₂CH₂OCH₃ Ph(4-OMe) Ph Ph(3-Cl) Ph(3-F)Ph(3-OMe) Ph(3,5-di-F) Q is S(O) H Et n-Pr OCH₂CH₂OCH₃ Ph(4-OMe) PhPh(3-Cl) Ph(3-F) Ph(3-OMe) Ph(3,5-di-F) Q is S(O)₂ H Et n-Pr OCH₂CH₂OCH₃Ph(4-OMe) Ph Ph(3-Cl) Ph(3-F) Ph(3-OMe) Ph(3,5-di-F)

TABLE 12 Table 12 is constructed the same as Table 11, except thestructure is replaced with

TABLE 13

R²⁴ R²⁴ R²⁴ R²⁴ R²⁴ Q is O H Et n-Pr OCH₂CH₂OCH₃ Ph(4-OMe) Ph Ph(3-Cl)Ph(3-F) Ph(3-OMe) Ph(3,5-di-F) Q is NCH₃ H Et n-Pr OCH₂CH₂OCH₃ Ph(4-OMe)Ph Ph(3-Cl) Ph(3-F) Ph(3-OMe) Ph(3,5-di-F) Q is S H Et n-Pr OCH₂CH₂OCH₃Ph(4-OMe) Ph Ph(3-Cl) Ph(3-F) Ph(3-OMe) Ph(3,5-di-F) Q is S(O) H Et n-PrOCH₂CH₂OCH₃ Ph(4-OMe) Ph Ph(3-Cl) Ph(3-F) Ph(3-OMe) Ph(3,5-di-F) Q isS(O)₂ H Et n-Pr OCH₂CH₂OCH₃ Ph(4-OMe) Ph Ph(3-Cl) Ph(3-F) Ph(3-OMe)Ph(3,5-di-F)

TABLE 14 Table 14 is constructed the same as Table 13, except thestructure is replaced with

TABLE 15 Table 15 is constructed the same as Table 13, except thestructure is replaced with

TABLE 16 Table 16 is constructed the same as Table 13, except thestructure is replaced with

TABLE 17 Table 17 is constructed the same as Table 13, except thestructure is replaced with

TABLE 18 Table 18 is constructed the same as Table 13, except thestructure is replaced with

TABLE 19

R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pent c-Pentn-Hex c-Hex Ph CH₂-c-Pr CH₂-c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph Ph(4-Me)CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂CH₂C≡CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe)CH₂SO₂-n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe)Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe) CH₂Ph(4-OMe) CH₂CH₂SMeCH₂SCH₂Ph CH₂SO₂Ph CH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-Cl)Ph(3,5-di-Cl) Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me)Ph(3,5-di-Me) CH₂-c-Hex Ph(2,3-di-F) Ph(2,4-di-F) Ph(2,5-di-F)Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl) Ph(3,5-di-F)isoxazolin-2-yl Ph(2-Cl) Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN) Ph(4-CN)Ph(2-F) Ph(3-F) Ph(4-F) CH₂S-n-Pr CH₂-c-Pent oxazolin-2-yl 2-pyridinyl3-pyridinyl 4-pyridinyl Ph(2-NO₂) Ph(3-NO₂) Ph(4-NO₂) Ph(2-CF₃)Ph(3-CF₃) Ph(4-CF₃) Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me)CH₂Ph(4-Me) CH₂Ph(2-Cl) CH₂Ph(3-Cl) CH₂Ph(4-Cl) thiazol-3-ylthiazol-2-yl thiazolin-2-yl thiazol-2-yl oxazol-2-yl CH₂CF₂CF₃ CH═CH₂CH₂(thf-2-yl) CH₂(3-methylisoxazolin-5-yl) isoxazolin-4-ylCH₂(3-methylisoxazol-5-yl) 5-methylisoxazol-3-yl 4-methyloxazol-2-yl4-methylthiazol-2-yl CH₂CH₂CH═CH₂ CH₂SO₂CH₂CH₃ CH₂CH₂SO₂Me CH₂OCH₂OCH₃3-methylthiazol-2-yl 5-chloropyridin-2-yl 5-methylpyridin-2-yl5-methoxypyridin-2-yl 6-methylpyridin-2-yl 6-methylpyridin-3-yl3-methoxypyridin-4-yl 3-methylpyridin-4-yl 3-chloropyridin-4-ylCH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ n-hept c-hept thp-4-yl thtp-4-ylPh(2,3-di-OMe) Ph(3,4-di-OMe) Ph(3,4-di-Me) Ph(3,4-di-F)Ph(3,4,5-tri-OMe) Ph(2-I) Ph(3-I) Ph(4-I) Ph(2-Et) Ph(3-Et) Ph(4-Et)CH₂CH₂OCH₂CH₃ CH(CH₃)CH₂OCH₃ Ph(2-OCF₃) Ph(3-OCF₃) Ph(4-OCF₃)Ph(2-Me-3-F) Ph(2-Me-4-F) Ph(2-Me-5-F) Ph(2-F-3-Me) Ph(2-F-4-Me)Ph(2-F-5-Me) Ph(3-F-4-Me) Ph(3-F-5-Me) Ph(3-Me-4-F) CH₂CH₂CH₂OCH₃CH₂CH₂CH₂OCH₂CH₃ CH₂(thp-2-yl) CH₂(thp-4-yl) CH₂CH₂CH═CH₂ CH₂C≡CHCH₂CH₂SCH₃ CH₂CH₂SOCH₃ CH₂CH₂SO₂CH₃ CH₂CH₂CH₂SCH₃ CH₂CH₂CH₂SOCH₃CH₂CH₂CH₂SO₂CH₃The present disclosure also includes Tables 1U through 57U, each ofwhich is constructed the same as Table 19 above except that the rowheading in Table 19 (i.e. “R² is Ph”) is replaced with the respectiverow headings shown below. For example, in Table 1U the row heading is“R² is Me”, and R¹ is as defined in Table 19 above. Thus, the firstentry in Table 1U specifically discloses a compound of Formula 1 whereinX is CH; Y is C(O); R¹ is Me; R² is Me; R³ is OH; A is A-1; B¹ is C-1;B² is C-3; B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2Uthrough 57U are constructed similarly.

Table Row Heading  1U R² is Me  2U R² is Et  3U R² is n-Pr  4U R² isc-Pr  5U R² is SMe  6U R² is SO₂Me  7U R² is CF₃  8U R² is Ph(2-Cl)  9UR² is Ph(3-Cl) 10U R² is Ph(4-Cl) 11U R² is Ph(2-Me) 12U R² is Ph(3-Me)13U R² is Ph(4-Me) 14U R² is Ph(2-OMe) 15U R² is Ph(3-OMe) 16U R² isPh(4-OMe) 17U R² is Ph(2-F) 18U R² is Ph(3-F) 19U R² is Ph(4-F) 20U R²is OMe 21U R² is OEt 22U R² is CH₂Ph 23U R² is 2-pyridinyl 24U R² is3-pyridinyl 25U R² is 4-pyridinyl 26U R² is H 27U R² is Ph(3,5-di-F) 28UR² is Ph(3,4-di-F) 29U R² is Ph(3,4,5-tri-F) 30U R² is Ph(2,3-di-F) 31UR² is Ph(3-CF₃) 32U R² is Ph(4-CF₃) 33U R² is Ph(3,5-di-CF₃) 34U R² isn-Bu 35U R² is CH₂OCH₃ 36U R² is CH₂CH₂OCH₃ 37U R² is CH₂CH₂CF₃ 38U R²is CH₂CF₃ 39U R² is n-pent 40U R² is c-pent 41U R² is c-Hex 42U R² isn-Hex 43U R² is thp-4-yl 44U R² is Ph(2-CN) 45U R² is Ph(3-CN) 46U R² isPh(4-CN) 47U R² is Ph(2-C≡CH) 48U R² is Ph(3-C≡CH) 49U R² is Ph(4-C≡CH)50U R² is Ph(3-Me, 2-F) 51U R² is Ph(3-Me-4-F) 52U R² is Ph(3-Me, 5-F)53U R² is Ph(3-Me, 6-F) 54U R² is Ph(3-F, 2-Me) 55U R² is Ph(3-F-4-Me)56U R² is Ph(3-F-5-Me) 57U R² is Ph(3-F, 6-Me)

TABLE 20 Table 20 is constructed the same as Table 19 except thestructure is replaced with

TABLE 21 Table 21 is constructed the same as Table 19 except thestructure is replaced with

TABLE 22 Table 22 is constructed the same as Table 19 except thestructure is replaced with

TABLE 23 Table 23 is constructed the same as Table 19 except thestructure is replaced with

TABLE 24 Table 24 is constructed the same as Table 19 except thestructure is replaced with

TABLE 25 Table 25 is constructed the same as Table 19 except thestructure is replaced with

TABLE 26 Table 26 is the same as Table 19 except the structure isreplaced with

TABLE 27

R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pent c-Pentn-Hex c-Hex Ph CH₂-c-Pr CH₂-c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph Ph(4-Me)CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂CH₂C≡CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe)CH₂SO₂-n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe)Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe) CH₂Ph(4-OMe) CH₂CH₂SMeCH₂SCH₂Ph CH₂SO₂Ph CH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-Cl)Ph(3,5-di-Cl) Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me)Ph(3,5-di-Me) CH₂-c-Hex Ph(2,3-di-F) Ph(2,4-di-F) Ph(2,5-di-F)Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl) Ph(3,5-di-F)isoxazolin-2-yl Ph(2-Cl) Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN) Ph(4-CN)Ph(2-F) Ph(3-F) Ph(4-F) CH₂S-n-Pr CH₂-c-Pent oxazolin-2-yl 2-pyridinyl3-pyridinyl 4-pyridinyl Ph(2-NO₂) Ph(3-NO₂) Ph(4-NO₂) Ph(2-CF₃)Ph(3-CF₃) Ph(4-CF₃) Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me)CH₂Ph(4-Me) CH₂Ph(2-Cl) CH₂Ph(3-Cl) CH₂Ph(4-Cl) thiazol-3-ylthiazol-2-yl thiazolin-2-yl thiazol-2-yl oxazol-2-yl CH₂CF₂CF₃ CH═CH₂CH₂(thf-2-yl) CH₂(3-methylisoxazolin-5-yl) isoxazolin-4-ylCH₂(3-methylisoxazol-5-yl) 5-methylisoxazol-3-yl 4-methyloxazol-2-yl4-methylthiazol-2-yl CH₂CH₂CH═CH₂ CH₂SO₂CH₂CH₃ CH₂CH₂SO₂Me CH₂OCH₂OCH₃3-methylthiazol-2-yl 5-chloropyridin-2-yl 5-methylpyridin-2-yl5-methoxypyridin-2-yl 6-methylpyridin-2-yl 6-methylpyridin-3-yl3-methoxypyridin-4-yl 3-methylpyridin-4-yl 3-chloropyridin-4-ylCH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ n-hept c-hept thp-4-yl thtp-4-ylPh(2,3-di-OMe) Ph(3,4-di-OMe) Ph(3,4-di-Me) Ph(3,4-di-F)Ph(3,4,5-tri-OMe) Ph(2-I) Ph(3-I) Ph(4-I) Ph(2-Et) Ph(3-Et) Ph(4-Et)CH₂CH₂OCH₂CH₃ CH(CH₃)CH₂OCH₃ Ph(2-OCF₃) Ph(3-OCF₃) Ph(4-OCF₃)Ph(2-Me-3-F) Ph(2-Me-4-F) Ph(2-Me-5-F) Ph(2-F-3-Me) Ph(2-F-4-Me)Ph(2-F-5-Me) Ph(3-F-4-Me) Ph(3-F-5-Me) Ph(3-Me-4-F) CH₂CH₂CH₂OCH₃CH₂CH₂CH₂OCH₂CH₃ CH₂(thp-2-yl) CH₂(thp-4-yl) CH₂CH₂CH═CH₂ CH₂C≡CHCH₂CH₂SCH₃ CH₂CH₂SOCH₃ CH₂CH₂SO₂CH₃ CH₂CH₂CH₂SCH₃ CH₂CH₂CH₂SOCH₃CH₂CH₂CH₂SO₂CH₃

The present disclosure also includes Tables 1BB through 57BB, each ofwhich is constructed the same as Table 27 above except that the rowheading in Table 27 (i.e. “R² is Ph”) is replaced with the respectiverow headings shown below. For example, in Table 1BB the row heading is“R² is Me”, and R¹ is as defined in Table 27 above. Thus, the firstentry in Table 1BB specifically discloses a compound of Formula 1wherein X is CH; Y is C(O); R¹ is Me; R² is Me; R³ is OH; A is A-1; B¹is C-1; B² is C-3; B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H.Tables 2BB through 57BB are constructed similarly.

Table Row Heading  1BB R² is Me  2BB R² is Et  3BB R² is n-Pr  4BB R² isc-Pr  5BB R² is SMe  6BB R² is SO₂Me  7BB R² is CF₃  8BB R² is Ph(2-Cl) 9BB R² is Ph(3-Cl) 10BB R² is Ph(4-Cl) 11BB R² is Ph(2-Me) 12BB R² isPh(3-Me) 13BB R² is Ph(4-Me) 14BB R² is Ph(2-OMe) 15BB R² is Ph(3-OMe)16BB R² is Ph(4-OMe) 17BB R² is Ph(2-F) 18BB R² is Ph(3-F) 19BB R² isPh(4-F) 20BB R² is OMe 21BB R² is OEt 22BB R² is CH₂Ph 23BB R² is2-pyridinyl 24BB R² is 3-pyridinyl 25BB R² is 4-pyridinyl 26BB H 27BBPh(3,5-di-F) 28BB Ph(3,4-di-F) 29BB Ph(3,4,5-tri-F) 30BB Ph(2,3-di-F)31BB Ph(3-CF₃) 32BB Ph(4-CF₃) 33BB Ph(3,5-di-CF₃) 34BB n-Bu 35BB CH₂OCH₃36BB CH₂CH₂OCH₃ 37BB CH₂CH₂CF₃ 38BB CH₂CF₃ 39BB n-pent 40BB c-pent 41BBc-Hex 42BB n-Hex 43BB thp-4-y1 44BB Ph(2-CN) 45BB Ph(3-CN) 46BB Ph(4-CN)47BB Ph(2-C≡CH) 48BB Ph(3-C≡CH) 49BB Ph(4-C≡CH) 50BB Ph(3-Me, 2-F) 51BBPh(3-Me-4-F) 52BB Ph(3-Me, 5-F) 53BB Ph(3-Me, 6-F) 54BB Ph(3-F, 2-Me)55BB Ph(3-F-4-Me) 56BB Ph(3-F-5-Me) 57BB Ph(3-F, 6-Me)

TABLE 28 Table 28 is constructed the same as Table 27 except thestructure is replaced with

TABLE 29 Table 29 is constructed the same as Table 27 except thestructure is replaced with

TABLE 30 Table 30 is constructed the same as Table 27 except thestructure is replaced with

TABLE 31 Table 31 is constructed the same as Table 27 except thestructure is replaced with

TABLE 32 Table 32 is constructed the same as Table 27 except thestructure is replaced with

TABLE 33 Table 32 is constructed the same as Table 27 except thestructure is replaced with

TABLE 34

R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu i-Bu s-Bu c-Bu t-Bu n-pentCH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂ CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂CH₂C≡CCH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ CH₂SO₂Ph CH₂SCH₂PhCH₂CH₂SEt Ph(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-Cl) Ph(3,5-di-Cl)Ph(2,3-di-Me) Ph(2,4-di-Me) Ph(2,5-di-Me) Ph(2,6-di-Me) Ph(2-Cl)Ph(3-Cl) Ph(4-Cl) Ph(2-Me) Ph(3-Me) CH₂OCH₃ CH₂CH═CH₂ Ph(2-OMe)Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(4-NO₂) Ph(2-CF₃) Ph(3-CF₃) Ph(4-CF₃)Ph(2-Br) Ph(3-Br) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me) CH₂Ph(4-Me)CH₂Ph(2-Cl) c-Pent n-Hex c-Hex Ph CH₂—c-Pr CH₂—c-Bu CH₂SPh CH₂SCH₃CH₂CF₃ CH₂Ph Ph(2,3-di-OMe) CH₂SO₂—n-Pr CH₂CH₂SO₂Et Ph(2,4-di-OMe)Ph(2,5-di-OMe) Ph(2,6-di-OMe) Ph(3,5-di-OMe) CH₂Ph(2-OMe) CH₂Ph(3-OMe)CH₂Ph(4-OMe) Ph(3,5-di-Me) CH₂—c-Hex Ph(2,3-di-F) Ph(2,4-di-F)Ph(2,5-di-F) Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl) Ph(3-NO₂)Ph(3-CN) Ph(4-CN) Ph(2-F) Ph(3-F) Ph(4-F) CH₂S—n-Pr CH₂—c-Pent CH₂CF₂CF₃CH═CH₂ Ph(2-NO₂) CH₂Ph(3-Cl) CH₂Ph(4-Cl) CH₂CH₂SO₂Me CH₂OCH₂OCH₃CH₂OCH₂CH₂OCH₃ CH₂C(CH₃)C(CH₃)₂ Ph(4-Me) CH₂CH₂SMe Ph(3,5-di-F)The present disclosure also includes Tables 1K through 4K, each of whichis constructed the same as Table 11 above except that the row heading inTable 11 (i.e. “R² is Ph”) is replaced with the respective row headingsshown below. For example, in Table 1K the row heading is “R² is Ph”, andR¹ is as defined in Table 11 above. Thus, the first entry in Table 1Kspecifically discloses a compound of Formula 1P wherein X is N, Y isC(O), R¹ is Me; R² is c-Pr; R³ is OH; A is A-1; B¹ is C-1; B² is C-3; B³is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ is H. Tables 2K through 4K areconstructed similarly.

Table Row Heading 1K R² is c-Pr 2K R² is SMe 3K R² is SO₂Me 4K R² is CF₃

TABLE 35

R² is Ph R¹ Me Et n-Pr i-Pr c-Pr n-Bu CH₂CHC(CH₃)₂ CH₂CH₂C≡CH CH₂CH═CCl₂CH₂CH═CF₂ CH₂CF═CF₂ CH₂CCl═CCl₂ CH₂SO₂Ph CH₂SCH₂Ph CH₂CH₂SEtPh(2,4-di-Cl) Ph(2,5-di-Cl) Ph(2,6-di-Cl) Ph(2-Cl) Ph(3-Cl) Ph(4-Cl)Ph(2-Me) Ph(3-Me) CH₂OCH₃ Ph(4-NO₂) Ph(2-CF₃) Ph(3-CF₃) Ph(4-CF₃)Ph(2-Br) Ph(3-Br) i-Bu s-Bu c-Bu t-Bu n-pent c-Pent n-Hex c-Hex PhCH₂—c-Pr CH₂—c-Bu CH₂SPh CH₂SCH₃ CH₂CF₃ CH₂Ph CH₂C≡CCH₃ CH₂OCH₂CH₃CH₂CH₂OCH₃ CH₂SO₂CH₃ CH₂SCH₂CH₃ Ph(2,3-di-OMe) CH₂SO₂—n-Pr CH₂CH₂SO₂EtPh(2,4-di-OMe) Ph(2,5-di-OMe) Ph(2,6-di-OMe) Ph(3,5-di-OMe) CH₂Ph(2-OMe)CH₂Ph(3-OMe) CH₂Ph(4-OMe) Ph(3,5-di-Cl) Ph(2,3-di-Me) Ph(2,4-di-Me)Ph(2,5-di-Me) Ph(2,6-di-Me) Ph(3,5-di-Me) CH₂—c-Hex Ph(2,3-di-F)Ph(2,4-di-F) Ph(2,5-di-F) Ph(2,6-di-F) CH₂CH₂CF₃ CH₂C≡CH Ph(2,3-di-Cl)Ph(3-NO₂) CH₂CH═CH₂ Ph(2-OMe) Ph(3-OMe) Ph(4-OMe) Ph(2-CN) Ph(3-CN)Ph(4-CN) Ph(2-F) Ph(3-F) Ph(4-F) CH₂S—n-Pr CH₂—c-Pent CH₂CF₂CF₃ CH═CH₂Ph(2-NO₂) Ph(4-Br) CH₂Ph(2-Me) CH₂Ph(3-Me) CH₂Ph(4-Me) CH₂Ph(2-Cl)CH₂Ph(3-Cl) CH₂Ph(4-Cl) CH₂CH₂SO₂Me CH₂OCH₂OCH₃ CH₂OCH₂CH₂OCH₃CH₂C(CH₃)C(CH₃)₂ Ph(4-Me) CH₂CH₂SMe Ph(3,5-di-F)The present disclosure also includes Tables 1L through 11L, each ofwhich is constructed the same as Table 12 above except that the rowheading in Table 12 (i.e. “R² is Ph”) is replaced with the respectiverow headings shown below. For example, in Table 1L the row heading is“R² is Ph”, and R¹ is as defined in Table 12 above. Thus, the firstentry in Table 1L specifically discloses a compound of Formula 1Pwherein X is CH; Y is S(O)₂; R¹ is Me and R² is c-Pr; R³ is OH; A isA-1; B¹ is C-1; B² is C-3; B³ is C-1; and each R¹⁴, R¹⁵, R¹⁸ and R¹⁹ isH. Tables 2L through 11L are constructed similarly.

Table Row Heading 1L R² is c-Pr 2L R² is n-Pr 3L R² is SMe 4L R² isSO₂Me 5L R² is CF₃ 6L R² Ph(2-Cl) 7L R² Ph(3-Cl) 8L R² is Ph(4-Cl) 9L R²is Ph(2-Me) 10L  R² is Ph(3-Me) 11L  R² is Ph(4-Me)

A compound of this invention will generally be used as a herbicidalactive ingredient in a composition, i.e. formulation, with at least oneadditional component selected from the group consisting of surfactants,solid diluents and liquid diluents, which serves as a carrier. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature.

Useful formulations include both liquid and solid compositions. Liquidcompositions include solutions (including emulsifiable concentrates),suspensions, emulsions (including microemulsions and/or suspoemulsions)and the like, which optionally can be thickened into gels. The generaltypes of aqueous liquid compositions are soluble concentrate, suspensionconcentrate, capsule suspension, concentrated emulsion, microemulsionand suspo-emulsion. The general types of nonaqueous liquid compositionsare emulsifiable concentrate, microemulsifiable concentrate, dispersibleconcentrate and oil dispersion.

The general types of solid compositions are dusts, powders, granules,pellets, prills, pastilles, tablets, filled films (including seedcoatings) and the like, which can be water-dispersible (“wettable”) orwater-soluble. Films and coatings formed from film-forming solutions orflowable suspensions are particularly useful for seed treatment. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. An emulsifiablegranule combines the advantages of both an emulsifiable concentrateformulation and a dry granular formulation. High-strength compositionsare primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable mediumbefore spraying. Such liquid and solid formulations are formulated to bereadily diluted in the spray medium, usually water. Spray volumes canrange from about from about one to several thousand liters per hectare,but more typically are in the range from about ten to several hundredliters per hectare. Sprayable formulations can be tank mixed with wateror another suitable medium for foliar treatment by aerial or groundapplication, or for application to the growing medium of the plant.Liquid and dry formulations can be metered directly into drip irrigationsystems or metered into the furrow during planting.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand Water- 0.001-90      0-99.999 0-15 soluble Granules, Tablets andPowders Oil Dispersions, Suspensions,  1-50 40-99 0-50 Emulsions,Solutions (including Emulsifiable Concentrates) Dusts  1-25 70-99 0-5 Granules and Pellets 0.001-99      5-99.999 0-15 High StrengthCompositions 90-99  0-10 0-2 

Solid diluents include, for example, clays such as bentonite,montmorillonite, attapulgite and kaolin, gypsum, cellulose, titaniumdioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose),silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodiumcarbonate and bicarbonate, and sodium sulfate. Typical solid diluentsare described in Watkins et al., Handbook of Insecticide Dust Diluentsand Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides(e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide,N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol,triethylene glycol, propylene glycol, dipropylene glycol, polypropyleneglycol, propylene carbonate, butylene carbonate, paraffins (e.g., whitemineral oils, normal paraffins, isoparaffins), alkylbenzenes,alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatichydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes,ketones such as cyclohexanone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexylacetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetateand isobornyl acetate, other esters such as alkylated lactate esters,dibasic esters and γ-butyrolactone, and alcohols, which can be linear,branched, saturated or unsaturated, such as methanol, ethanol,n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol,2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol,cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol,cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol and benzylalcohol. Liquid diluents also include glycerol esters of saturated andunsaturated fatty acids (typically C₆-C₂₂), such as plant seed and fruitoils (e.g., oils of olive, castor, linseed, sesame, corn (maize),peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed,coconut and palm kernel), animal-sourced fats (e.g., beef tallow, porktallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquiddiluents also include alkylated fatty acids (e.g., methylated,ethylated, butylated) wherein the fatty acids may be obtained byhydrolysis of glycerol esters from plant and animal sources, and can bepurified by distillation. Typical liquid diluents are described inMarsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

The solid and liquid compositions of the present invention often includeone or more surfactants. When added to a liquid, surfactants (also knownas “surface-active agents”) generally modify, most often reduce, thesurface tension of the liquid. Depending on the nature of thehydrophilic and lipophilic groups in a surfactant molecule, surfactantscan be useful as wetting agents, dispersants, emulsifiers or defoamingagents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionicsurfactants useful for the present compositions include, but are notlimited to: alcohol alkoxylates such as alcohol alkoxylates based onnatural and synthetic alcohols (which may be branched or linear) andprepared from the alcohols and ethylene oxide, propylene oxide, butyleneoxide or mixtures thereof; amine ethoxylates, alkanolamides andethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylatedsoybean, castor and rapeseed oils; alkylphenol alkoxylates such asoctylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenolethoxylates and dodecyl phenol ethoxylates (prepared from the phenolsand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); block polymers prepared from ethylene oxide or propylene oxideand reverse block polymers where the terminal blocks are prepared frompropylene oxide; ethoxylated fatty acids; ethoxylated fatty esters andoils; ethoxylated methyl esters; ethoxylated tristyrylphenol (includingthose prepared from ethylene oxide, propylene oxide, butylene oxide ormixtures thereof); fatty acid esters, glycerol esters, lanolin-basedderivatives, polyethoxylate esters such as polyethoxylated sorbitanfatty acid esters, polyethoxylated sorbitol fatty acid esters andpolyethoxylated glycerol fatty acid esters; other sorbitan derivativessuch as sorbitan esters; polymeric surfactants such as randomcopolymers, block copolymers, alkyd peg (polyethylene glycol) resins,graft or comb polymers and star polymers; polyethylene glycols (pegs);polyethylene glycol fatty acid esters; silicone-based surfactants; andsugar-derivatives such as sucrose esters, alkyl polyglycosides and alkylpolysaccharides.

Useful anionic surfactants include, but are not limited to: alkylarylsulfonic acids and their salts; carboxylated alcohol or alkylphenolethoxylates; diphenyl sulfonate derivatives; lignin and ligninderivatives such as lignosulfonates; maleic or succinic acids or theiranhydrides; olefin sulfonates; phosphate esters such as phosphate estersof alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates andphosphate esters of styryl phenol ethoxylates; protein-basedsurfactants; sarcosine derivatives; styryl phenol ether sulfate;sulfates and sulfonates of oils and fatty acids; sulfates and sulfonatesof ethoxylated alkylphenols; sulfates of alcohols; sulfates ofethoxylated alcohols; sulfonates of amines and amides such asN,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, anddodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes;sulfonates of naphthalene and alkyl naphthalene; sulfonates offractionated petroleum; sulfosuccinamates; and sulfosuccinates and theirderivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides andethoxylated amides; amines such as N-alkyl propanediamines,tripropylenetriamines and dipropylenetetramines, and ethoxylated amines,ethoxylated diamines and propoxylated amines (prepared from the aminesand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); amine salts such as amine acetates and diamine salts;quaternary ammonium salts such as quaternary salts, ethoxylatedquaternary salts and diquaternary salts; and amine oxides such asalkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic andanionic surfactants or mixtures of nonionic and cationic surfactants.Nonionic, anionic and cationic surfactants and their recommended usesare disclosed in a variety of published references includingMcCutcheon's Emulsifiers and Detergents, annual American andInternational Editions published by McCutcheon's Division, TheManufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopediaof Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; andA. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition,John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliariesand additives, known to those skilled in the art as formulation aids(some of which may be considered to also function as solid diluents,liquid diluents or surfactants). Such formulation auxiliaries andadditives may control: pH (buffers), foaming during processing(antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2. Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typicallyincorporated into the present compositions by dissolving the activeingredient in a solvent or by grinding in a liquid or dry diluent.Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. If the solvent of a liquid compositionintended for use as an emulsifiable concentrate is water-immiscible, anemulsifier is typically added to emulsify the active-containing solventupon dilution with water. Active ingredient slurries, with particlediameters of up to 2,000 μm can be wet milled using media mills toobtain particles with average diameters below 3 μm. Aqueous slurries canbe made into finished suspension concentrates (see, for example, U.S.Pat. No. 3,060,084) or further processed by spray drying to formwater-dispersible granules. Dry formulations usually require dry millingprocesses, which produce average particle diameters in the 2 to 10 μmrange. Dusts and powders can be prepared by blending and usuallygrinding (such as with a hammer mill or fluid-energy mill). Granules andpellets can be prepared by spraying the active material upon preformedgranular carriers or by agglomeration techniques. See Browning,“Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry'sChemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963,pages 8-57 and following, and WO 91/13546. Pellets can be prepared asdescribed in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. No.4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can beprepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB2,095,558 and U.S. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food-Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developmentsin formulation technology, PJB Publications, Richmond, UK, 2000.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A-B. Without further elaboration, it isbelieved that one skilled in the art using the preceding description canutilize the present invention to its fullest extent. The followingExamples are, therefore, to be construed as merely illustrative, and notlimiting of the disclosure in any way whatsoever. Percentages are byweight except where otherwise indicated.

Example A

High Strength Concentrate Compound 4 98.5% silica aerogel 0.5% syntheticamorphous fine silica 1.0%

Example B

Wettable Powder Compound 2 65.0% dodecylphenol polyethylene glycol ether2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0%montmorillonite (calcined) 23.0%

Example C

Granule Compound 12 10.0% attapulgite granules (low volatile matter,0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet Compound 8 25.0% anhydrous sodium sulfate 10.0% crudecalcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%

Example E

Emulsifiable Concentrate Compound 2 10.0% polyoxyethylene sorbitolhexoleate 20.0% C₆-C₁₀ fatty acid methyl ester 70.0%

Example F

Microemulsion Compound 12 5.0% polyvinylpyrrolidone-vinyl acetatecopolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% Water20.0%

These compounds generally show highest activity for early postemergenceweed control (i.e. applied when the emerged weed seedlings are stillyoung) and preemergence weed control (i.e. applied before weed seedlingsemerge from the soil). Many of them have utility for broad-spectrum pre-and/or postemergence weed control in areas where complete control of allvegetation is desired such as around fuel storage tanks, industrialstorage areas, parking lots, drive-in theaters, air fields, river banks,irrigation and other waterways, around billboards and highway andrailroad structures. Many of the compounds of this invention, by virtueof selective metabolism in crops versus weeds, or by selective activityat the locus of physiological inhibition in crops and weeds, or byselective placement on or within the environment of a mixture of cropsand weeds, are useful for the selective control of grass and broadleafweeds within a crop/weed mixture. One skilled in the art will recognizethat the preferred combination of these selectivity factors within acompound or group of compounds can readily be determined by performingroutine biological and/or biochemical assays. Compounds of thisinvention may show tolerance to important agronomic crops including, butnot limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn(maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato,potato, perennial plantation crops including coffee, cocoa, oil palm,rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana,plantain, pineapple, hops, tea and forests such as eucalyptus andconifers (e.g., loblolly pine), and turf species (e.g., Kentuckybluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass).Compounds of the invention are particularly useful for selective controlof weeds in wheat, barley, and particularly maize, soybean, cotton andperennial plantation crops such as sugarcane and citrus. Compounds ofthis invention can be used in crops genetically transformed or bred toincorporate resistance to herbicides, express proteins toxic toinvertebrate pests (such as Bacillus thuringiensis toxin), and/orexpress other useful traits. Those skilled in the art will appreciatethat not all compounds are equally effective against all weeds.Alternatively, the subject compounds are useful to modify plant growth.

As the compounds of the invention have both postemergent and preemergentherbicidal activity, to control undesired vegetation by killing orinjuring the vegetation or reducing its growth, the compounds can beusefully applied by a variety of methods involving contacting aherbicidally effective amount of a compound of the invention, or acomposition comprising said compound and at least one of a surfactant, asolid diluent or a liquid diluent, to the foliage or other part of theundesired vegetation or to the environment of the undesired vegetationsuch as the soil or water in which the undesired vegetation is growingor which surrounds the seed or other propagule of the undesiredvegetation.

A herbicidally effective amount of the compounds of this invention isdetermined by a number of factors. These factors include: formulationselected, method of application, amount and type of vegetation present,growing conditions, etc. In general, a herbicidally effective amount ofa compound of this invention is about 0.001 to 20 kg/ha with a typicalrange of about 0.004 to 1 kg/ha. One skilled in the art can easilydetermine the herbicidally effective amount necessary for the desiredlevel of weed control.

Compounds of this invention can also be mixed with one or more otherbiologically active compounds or agents including herbicides, herbicidesafeners, fungicides, insecticides, nematocides, bactericides,acaricides, growth regulators such as insect molting inhibitors androoting stimulants, chemosterilants, semiochemicals, repellents,attractants, pheromones, feeding stimulants, plant nutrients, otherbiologically active compounds or entomopathogenic bacteria, virus orfungi to form a multi-component pesticide giving an even broaderspectrum of agricultural protection. Mixtures of the compounds of theinvention with other herbicides can broaden the spectrum of activityagainst additional weed species, and suppress the proliferation of anyresistant biotypes. Thus the present invention also pertains to acomposition comprising a compound of Formula 1 (in a herbicidallyeffective amount) and at least one additional biologically activecompound or agent (in a biologically effective amount) and can furthercomprise at least one of a surfactant, a solid diluent or a liquiddiluent. The other biologically active compounds or agents can beformulated in compositions comprising at least one of a surfactant,solid or liquid diluent. For mixtures of the present invention, one ormore other biologically active compounds or agents can be formulatedtogether with a compound of Formula 1, to form a premix, or one or moreother biologically active compounds or agents can be formulatedseparately from the compound of Formula 1, and the formulations combinedtogether before application (e.g., in a spray tank) or, alternatively,applied in succession.

A mixture of one or more of the following herbicides with a compound ofthis invention may be particularly useful for weed control: acetochlor,acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal),alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron,aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts(e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate,anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin,benazolin-ethyl, bencarbazone, benfluralin, benfuresate,bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap,bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt,bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate,butachlor, butafenacil, butamifos, butralin, butroxydim, butylate,cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen,chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon,chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron,chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin,cinosulfuron, clefoxydim, clethodim, clodinafop-propargyl, clomazone,clomeprop, clopyralid, clopyralid-olamine, cloransulam-methyl,cumyluron, cyanazine, cycloate, cyclosulfamuron, cycloxydim,cyhalofop-butyl, 2,4-D and its butotyl, butyl, isoctyl and isopropylesters and its dimethylammonium, diolamine and trolamine salts,daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DB and itsdimethylammonium, potassium and sodium salts, desmedipham, desmetryn,dicamba and its diglycolammonium, dimethylammonium, potassium and sodiumsalts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam,difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron,dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,dimethipin, dimethylarsinic acid and its sodium salt, dinitramine,dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC,endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl,ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid,fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide,fenuron, fenuron-TCA, flamprop-methyl, flamprop-M-isopropyl,flamprop-M-methyl, flazasulfuron, florasulam, fluazifop-butyl,fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron,fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam,flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl,flupoxam, flupyrsulfuron-methyl and its sodium salt, flurenol,flurenol-butyl, fluridone, flurochloridone, fluroxypyr, flurtamone,fluthiacet-methyl, fomesafen, foramsulfuron, fosamine-ammonium,glufosinate, glufosinate-ammonium, glyphosate and its salts such asammonium, isopropylammonium, potassium, sodium (including sesquisodium)and trimesium (alternatively named sulfosate), halo sulfuron-methyl,haloxyfop-etotyl, haloxyfop-methyl, hexazinone, imazamethabenz-methyl,imazamox, imazapic, imazapyr, imazaquin, imazaquin-ammonium,imazethapyr, imazethapyr-ammonium, imazosulfuron, indanofan,iodosulfuron-methyl, ioxynil, ioxynil octanoate, ioxynil-sodium,isoproturon, isouron, isoxaben, isoxaflutole, isoxachlortole, lactofen,lenacil, linuron, maleic hydrazide, MCPA and its salts (e.g.,MCPA-dimethylammonium, MCPA-potassium and MCPA-sodium, esters (e.g.,MCPA-2-ethylhexyl, MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl),MCPB and its salts (e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl),mecoprop, mecoprop-P, mefenacet, mefluidide, mesosulfuron-methyl,mesotrione, metam-sodium, metamifop, metamitron, metazachlor,metazosulfuron, methabenzthiazuron, methylarsonic acid and its calcium,monoammonium, monosodium and disodium salts, methyldymron, metobenzuron,metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron,metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide,napropamide, naptalam, neburon, nicosulfuron, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonicacid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone,pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium,picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl,prodiamine, profoxydim, prometon, prometryn, propachlor, propanil,propaquizafop, propazine, propham, propisochlor, propoxycarbazone,propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl,pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen,pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid,pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium,pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine,quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron,saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione,sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA,TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn,thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl,thiobencarb, tiocarbazil, topramezone, tralkoxydim, tri-allate,triasulfuron, triaziflam, tribenuron-methyl, triclopyr,triclopyr-butotyl, triclopyr-triethylammonium, tridiphane, trietazine,trifloxysulfuron, trifluralin, triflusulfuron-methyl, tritosulfuron andvernolate. Other herbicides also include bioherbicides such asAlternaria destruens Simmons, Colletotrichum gloeosporiodes (Penz.)Penz. & Sacc., Drechsiera monoceras (MTB-951), Myrothecium verrucaria(Albertini & Schweinitz) Ditmar: Fries, Phytophthora palmivora (Butl.)Butl. and Puccinia thlaspeos Schub.

Compounds of this invention can also be used in combination with plantgrowth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine,epocholeone, gibberellic acid, gibberellin A₄ and A₇, harpin protein,mepiquat chloride, prohexadione calcium, prohydrojasmon, sodiumnitrophenolate and trinexapac-methyl, and plant growth modifyingorganisms such as Bacillus cereus strain BP01.

General references for agricultural protectants (i.e. herbicides,herbicide safeners, insecticides, fungicides, nematocides, acaricidesand biological agents) include The Pesticide Manual, 13th Edition, C. D.S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K.,2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed.,British Crop Protection Council, Farnham, Surrey, U.K., 2001.

For embodiments where one or more of these various mixing partners areused, the weight ratio of these various mixing partners (in total) tothe compound of Formula 1 is typically between about 1:3000 and about3000:1. Of note are weight ratios between about 1:300 and about 300:1(for example ratios between about 1:30 and about 30:1). One skilled inthe art can easily determine through simple experimentation thebiologically effective amounts of active ingredients necessary for thedesired spectrum of biological activity. It will be evident thatincluding these additional components may expand the spectrum of weedscontrolled beyond the spectrum controlled by the compound of Formula 1alone.

In certain instances, combinations of a compound of this invention withother biologically active (particularly herbicidal) compounds or agents(i.e. active ingredients) can result in a greater-than-additive (i.e.synergistic) effect on weeds and/or a less-than-additive effect (i.e.safening) on crops or other desirable plants. Reducing the quantity ofactive ingredients released in the environment while ensuring effectivepest control is always desirable. Ability to use greater amounts ofactive ingredients to provide more effective weed control withoutexcessive crop injury is also desirable. When synergism of herbicidalactive ingredients occurs on weeds at application rates givingagronomically satisfactory levels of weed control, such combinations canbe advantageous for reducing crop production cost and decreasingenvironmental load. When safening of herbicidal active ingredientsoccurs on crops, such combinations can be advantageous for increasingcrop protection by reducing weed competition.

Of note is a combination of a compound of the invention with at leastone other herbicidal active ingredient. Of particular note is such acombination where the other herbicidal active ingredient has differentsite of action from the compound of the invention. In certain instances,a combination with at least one other herbicidal active ingredienthaving a similar spectrum of control but a different site of action willbe particularly advantageous for resistance management. Thus, acomposition of the present invention can further comprise (in aherbicidally effective amount) at least one additional herbicidal activeingredient having a similar spectrum of control but a different site ofaction.

Compounds of this invention can also be used in combination withherbicide safeners such as allidochlor, benoxacor, BCS(1-bromo-4-[(chloromethyl)sulfonyl]benzene), cloquintocet-mexyl,cyometrinil, cyprosulfonamide, dichlormid,4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660),2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), dicyclonon,dietholate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim,furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate,methoxyphenone ((4-methoxy-3-methylphenyl)(3-methylphenyl)methanone),naphthalic anhydride (1,8-naphthalic anhydride) and oxabetrinil toincrease safety to certain crops. Antidotally effective amounts of theherbicide safeners can be applied at the same time as the compounds ofthis invention, or applied as seed treatments. Therefore an aspect ofthe present invention relates to a herbicidal mixture comprising acompound of this invention and an antidotally effective amount of aherbicide safener. Seed treatment is particularly useful for selectiveweed control, because it physically restricts antidoting to the cropplants. Therefore a particularly useful embodiment of the presentinvention is a method for selectively controlling the growth ofundesired vegetation in a crop comprising contacting the locus of thecrop with a herbicidally effective amount of a compound of thisinvention wherein seed from which the crop is grown is treated with anantidotally effective amount of safener. Antidotally effective amountsof safeners can be easily determined by one skilled in the art throughsimple experimentation.

Of note is a composition comprising a compound of the invention (in aherbicidally effective amount), at least one additional activeingredient selected from the group consisting of other herbicides andherbicide safeners (in an effective amount), and at least one componentselected from the group consisting of surfactants, solid diluents andliquid diluents.

Preferred for better control of undesired vegetation (e.g., lower userate such as from synergism, broader spectrum of weeds controlled, orenhanced crop safety) or for preventing the development of resistantweeds are mixtures of a compound of this invention with a herbicideselected from the group consisting of 2,4-D, ametryne,aminocyclopyrachlor, aminopyralid, atrazine, bromacil, bromoxynil,bromoxynil octanoate, carfentrazone-ethyl, chlorimuron-ethyl,chlorsulfuron, clopyralid, clopyralid-olamine, dicamba and itsdiglycolammonium, dimethylammonium, potassium and sodium salts,diflufenican, dimethenamid, dimethenamid-P, diuron, florasulam,flufenacet, flumetsulam, flumioxazin, flupyrsulfuron-methyl,flupyrsulfuron-methyl-sodium, fluroxypyr, glyphosate (particularlyglyphosate-isopropylammonium, glyphosate-sodium, glyphosate-potassium,glyphosate-trimesium), hexazinone, imazamethabenz-methyl, imazaquin,imazethapyr, iodosulfuron-methyl, lactofen, lenacil, linuron, MCPA andits dimethylammonium, potassium and sodium salts, MCPA-isoctyl,MCPA-thioethyl, mesosulfuron-methyl, S-metolachlor, metribuzin,metsulfuron-methyl, nicosulfuron, oxyfluorfen, pendimethalin, pinoxaden,pronamide, prosulfuron, pyroxasulfone, pyroxsulam, quinclorac,rimsulfuron, saflufenacil, sulfentrazone, thifensulfuron-methyl,triasulfuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, andtriclopyr-triethylammonium. Specifically preferred mixtures (compoundnumbers refer to compounds in Index Table A) are selected from thegroup: compound 2 and 2,4-D; compound 4 and 2,4-D; compound 8 and 2,4-D;compound 12 and 2,4-D; compound 2 and ametryne; compound 4 and ametryne;compound 8 and ametryne; compound 12 and ametryne; compound 2 andaminocyclopyrachlor; compound 4 and aminocyclopyrachlor; compound 8 andaminocyclopyrachlor; compound 12 and aminocyclopyrachlor; compound 2 andaminopyralid; compound 4 and aminopyralid; compound 8 and aminopyralid;compound 12 and aminopyralid; compound 2 and atrazine; compound 4 andatrazine; compound 8 and atrazine; compound 12 and atrazine; compound 2and bromacil; compound 4 and bromacil; compound 8 and bromacil; compound12 and bromacil; compound 2 and bromoxynil; compound 4 and bromoxynil;compound 8 and bromoxynil; compound 12 and bromoxynil; compound 2 andbromoxynil octanoate; compound 4 and bromoxynil octanoate; compound 8and bromoxynil octanoate; compound 12 and bromoxynil octanoate; compound2 and carfentrazone-ethyl; compound 4 and carfentrazone-ethyl; compound8 and carfentrazone-ethyl; compound 12 and carfentrazone-ethyl; compound2 and chlorimuron-ethyl; compound 4 and chlorimuron-ethyl; compound 8and chlorimuron-ethyl; compound 12 and chlorimuron-ethyl; compound 2 andchlorsulfuron; compound 4 and chlorsulfuron; compound 8 andchlorsulfuron; compound 12 and chlorsulfuron; compound 2 and clopyralid;compound 4 and clopyralid; compound 8 and clopyralid; compound 12 andclopyralid; compound 2 and clopyralid-olamine; compound 4 andclopyralid-olamine; compound 8 and clopyralid-olamine; compound 12 andclopyralid-olamine; compound 2 and dicamba; compound 4 and dicamba;compound 8 and dicamba; compound 12 and dicamba; compound 2 anddiflufenican; compound 4 and diflufenican; compound 8 and diflufenican;compound 12 and diflufenican; compound 2 and dimethenamid; compound 4and dimethenamid; compound 8 and dimethenamid; compound 12 anddimethenamid; compound 2 and dimethenamid-P; compound 4 anddimethenamid-P; compound 8 and dimethenamid-P; compound 12 anddimethenamid-P; compound 2 and diuron; compound 4 and diuron; compound 8and diuron; compound 12 and diuron; compound 2 and florasulam; compound4 and florasulam; compound 8 and florasulam; compound 12 and florasulam;compound 2 and flufenacet; compound 4 and flufenacet; compound 8 andflufenacet; compound 12 and flufenacet; compound 2 and flumetsulam;compound 4 and flumetsulam; compound 8 and flumetsulam; compound 12 andflumetsulam; compound 2 and flumioxazin; compound 4 and flumioxazin;compound 8 and flumioxazin; compound 12 and flumioxazin; compound 2 andflupyrsulfuron-methyl; compound 4 and flupyrsulfuron-methyl; compound 8and flupyrsulfuron-methyl; compound 12 and flupyrsulfuron-methyl;compound 2 and flupyrsulfuron-methyl-sodium; compound 4 andflupyrsulfuron-methyl-sodium; compound 8 andflupyrsulfuron-methyl-sodium; compound 12 andflupyrsulfuron-methyl-sodium; compound 2 and fluroxypyr; compound 4 andfluroxypyr; compound 8 and fluroxypyr; compound 12 and fluroxypyr;compound 2 and glyphosate; compound 4 and glyphosate; compound 8 andglyphosate; compound 12 and glyphosate; compound 2 and hexazinone;compound 4 and hexazinone; compound 8 and hexazinone; compound 12 andhexazinone; compound 2 and imazamethabenz-methyl; compound 4 andimazamethabenz-methyl; compound 8 and imazamethabenz-methyl; compound 12and imazamethabenz-methyl; compound 2 and imazaquin; compound 4 andimazaquin; compound 8 and imazaquin; compound 12 and imazaquin; compound2 and imazethapyr; compound 4 and imazethapyr; compound 8 andimazethapyr; compound 12 and imazethapyr; compound 2 andiodosulfuron-methyl; compound 4 and iodosulfuron-methyl; compound 8 andiodosulfuron-methyl; compound 12 and iodosulfuron-methyl; compound 2 andlactofen; compound 4 and lactofen; compound 8 and lactofen; compound 12and lactofen; compound 2 and lenacil; compound 4 and lenacil; compound 8and lenacil; compound 12 and lenacil; compound 2 and linuron; compound 4and linuron; compound 8 and linuron; compound 12 and linuron; compound 2and MCPA; compound 4 and MCPA; compound 8 and MCPA; compound 12 andMCPA; compound 2 and MCPA-isoctyl; compound 4 and MCPA-isoctyl; compound8 and MCPA-isoctyl; compound 12 and MCPA-isoctyl; compound 2 andMCPA-thioethyl; compound 4 and MCPA-thioethyl; compound 8 andMCPA-thioethyl; compound 12 and MCPA-thioethyl; compound 2 andmesosulfuron-methyl; compound 4 and mesosulfuron-methyl; compound 8 andmesosulfuron-methyl; compound 12 and mesosulfuron-methyl; compound 2 andS-metolachlor; compound 4 and S-metolachlor; compound 8 andS-metolachlor; compound 12 and S-metolachlor; compound 2 and metribuzin;compound 4 and metribuzin; compound 8 and metribuzin; compound 12 andmetribuzin; compound 2 and metsulfuron-methyl; compound 4 andmetsulfuron-methyl; compound 8 and metsulfuron-methyl; compound 12 andmetsulfuron-methyl; compound 2 and nicosulfuron; compound 4 andnicosulfuron; compound 8 and nicosulfuron; compound 12 and nicosulfuron;compound 2 and oxyfluorfen; compound 4 and oxyfluorfen; compound 8 andoxyfluorfen; compound 12 and oxyfluorfen; compound 2 and pendimethalin;compound 4 and pendimethalin; compound 8 and pendimethalin; compound 12and pendimethalin; compound 2 and pinoxaden; compound 4 and pinoxaden;compound 8 and pinoxaden; compound 12 and pinoxaden; compound 2 andpronamide; compound 4 and pronamide; compound 8 and pronamide; compound12 and pronamide; compound 2 and prosulfuron; compound 4 andprosulfuron; compound 8 and prosulfuron; compound 12 and prosulfuron;compound 2 and pyroxasulfone; compound 4 and pyroxasulfone; compound 8and pyroxasulfone; compound 12 and pyroxasulfone; compound 2 andpyroxsulam; compound 4 and pyroxsulam; compound 8 and pyroxsulam;compound 12 and pyroxsulam; compound 2 and quinclorac; compound 4 andquinclorac; compound 8 and quinclorac; compound 12 and quinclorac;compound 2 and rimsulfuron; compound 4 and rimsulfuron; compound 8 andrimsulfuron; compound 12 and rimsulfuron; compound 2 and saflufenacil;compound 4 and saflufenacil; compound 8 and saflufenacil; compound 12and saflufenacil; compound 2 and sulfentrazone; compound 4 andsulfentrazone; compound 8 and sulfentrazone; compound 12 andsulfentrazone; compound 2 and thifensulfuron-methyl; compound 4 andthifensulfuron-methyl; compound 8 and thifensulfuron-methyl; compound 12and thifensulfuron-methyl; compound 2 and triasulfuron; compound 4 andtriasulfuron; compound 8 and triasulfuron; compound 12 and triasulfuron;compound 2 and tribenuron-methyl; compound 4 and tribenuron-methyl;compound 8 and tribenuron-methyl; compound 12 and tribenuron-methyl;compound 2 and triclopyr; compound 4 and triclopyr; compound 8 andtriclopyr; compound 12 and triclopyr; compound 2 and triclopyr-butotyl;compound 4 and triclopyr-butotyl; compound 8 and triclopyr-butotyl;compound 12 and triclopyr-butotyl; compound 2 andtriclopyr-triethylammonium; compound 4 and triclopyr-triethylammonium;compound 8 and triclopyr-triethylammonium; compound 12 andtriclopyr-triethylammonium.

Table A1 lists specific combinations of a compound of Formula 1 (i.e.Component (a)) with an additional active ingredient (i.e. Component (b))illustrative of the mixtures, compositions and methods of the presentinvention. The first column of Table A1 lists compound 45 as theillustrative compound of Formula 1. The second column of Table A1 liststhe specific Component (b) compound (e.g., “2,4-D” in the first line).The third, fourth and fifth columns of Table A1 lists ranges of weightratios for rates at which the Component (b) compound is typicallyapplied to a field-grown crop relative to Component (a). Thus, forexample, the first line of Table A1 specifically discloses thecombination of Component (a) with 2,4-D is typically applied in a weightratio between 1:192 to 6:1. The remaining lines of Table A1 are to beconstrued similarly.

TABLE A1 Typical More Typical Most Typical Component (a) Component (b)Weight Ratio Weight Ratio Weight Ratio Compound 47 2,4-D 1:192 to 6:1 1:64 to 2:1  1:24 to 1:3  Compound 47 acetochlor 1:768 to 2:1  1:256 to1:2  1:96 to 1:11 Compound 47 acifluorfen 1:96 to 12:1 1:32 to 4:1  1:12to 1:2  Compound 47 aclonifen 1:857 to 2:1  1:285 to 1:3  1:107 to 1:12 Compound 47 alachlor 1:768 to 2:1  1:256 to 1:2  1:96 to 1:11 Compound47 ametryn 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47amicarbazone 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3  Compound 47amidosulfuron  1:6 to 168:1  1:2 to 56:1  1:1 to 11:1 Compound 47aminocyclopyrachlor 1:48 to 24:1 1:16 to 8:1  1:6 to 2:1 Compound 47aminopyralid 1:20 to 56:1  1:6 to 19:1 1:2 to 4:1 Compound 47 amitrole1:768 to 2:1  1:256 to 1:2  1:96 to 1:11 Compound 47 anilofos 1:96 to12:1 1:32 to 4:1  1:12 to 1:2  Compound 47 asulam 1:960 to 2:1  1:320 to1:3  1:120 to 1:14  Compound 47 atrazine 1:192 to 6:1  1:64 to 2:1  1:24to 1:3  Compound 47 azimsulfuron  1:6 to 168:1  1:2 to 56:1  1:1 to 11:1Compound 47 beflubutamid 1:342 to 4:1  1:114 to 2:1  1:42 to 1:5 Compound 47 benfuresate 1:617 to 2:1  1:205 to 1:2  1:77 to 1:9 Compound 47 bensulfuron 1:25 to 45:1  1:8 to 15:1 1:3 to 3:1 Compound 47bentazon 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3  Compound 47benzobicyclon 1:85 to 14:1 1:28 to 5:1  1:10 to 1:2  Compound 47benzofenap 1:257 to 5:1  1:85 to 2:1  1:32 to 1:4  Compound 47bicyclopyrone 1:42 to 27:1 1:14 to 9:1  1:5 to 2:1 Compound 47 bifenox1:257 to 5:1  1:85 to 2:1  1:32 to 1:4  Compound 47 bispyribac-sodium 1:10 to 112:1  1:3 to 38:1 1:1 to 7:1 Compound 47 bromacil 1:384 to3:1  1:128 to 1:1  1:48 to 1:6  Compound 47 bromobutide 1:384 to 3:1 1:128 to 1:1  1:48 to 1:6  Compound 47 bromoxynil 1:96 to 12:1 1:32 to4:1  1:12 to 1:2  Compound 47 butachlor 1:768 to 2:1  1:256 to 1:2  1:96to 1:11 Compound 47 butafenacil 1:42 to 27:1 1:14 to 9:1  1:5 to 2:1Compound 47 butylate 1:1542 to 1:2   1:514 to 1:5  1:192 to 1:22 Compound 47 carfenstrole 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3 Compound 47 carfentrazone 1:128 to 9:1  1:42 to 3:1  1:16 to 1:2 Compound 47 chlorimuron  1:8 to 135:1  1:2 to 45:1 1:1 to 9:1 Compound47 chlorotoluron 1:768 to 2:1  1:256 to 1:2  1:96 to 1:11 Compound 47chlorsulfuron  1:6 to 168:1  1:2 to 56:1  1:1 to 11:1 Compound 47cincosulfuron 1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound 47cinidon-ethyl 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47cinmethylin 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 47 clethodim1:48 to 24:1 1:16 to 8:1  1:6 to 2:1 Compound 47 clodinafop 1:20 to 56:1 1:6 to 19:1 1:2 to 4:1 Compound 47 clomazone 1:384 to 3:1  1:128 to1:1  1:48 to 1:6  Compound 47 clomeprop 1:171 to 7:1  1:57 to 3:1  1:21to 1:3  Compound 47 clopyralid 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3 Compound 47 cloransulam 1:12 to 96:1  1:4 to 32:1 1:1 to 6:1 Compound 47cumyluron 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47 cyanazine1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47 cyclosulfamuron1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound 47 cycloxydim 1:96 to 12:11:32 to 4:1  1:12 to 1:2  Compound 47 cyhalofop 1:25 to 45:1  1:8 to15:1 1:3 to 3:1 Compound 47 daimuron 1:192 to 6:1  1:64 to 2:1  1:24 to1:3  Compound 47 desmedipham 1:322 to 4:1  1:107 to 2:1  1:40 to 1:5 Compound 47 dicamba 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3  Compound 47dichlobenil 1:1371 to 1:2   1:457 to 1:4  1:171 to 1:20  Compound 47dichlorprop 1:925 to 2:1  1:308 to 1:3  1:115 to 1:13  Compound 47diclofop 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47 diclosulam 1:10 to 112:1  1:3 to 38:1 1:1 to 7:1 Compound 47 difenzoquat 1:288 to4:1  1:96 to 2:1  1:36 to 1:4  Compound 47 diflufenican 1:857 to 2:1 1:285 to 1:3  1:107 to 1:12  Compound 47 diflufenzopyr 1:12 to 96:1  1:4to 32:1 1:1 to 6:1 Compound 47 dimethachlor 1:768 to 2:1  1:256 to 1:2 1:96 to 1:11 Compound 47 dimethametryn 1:192 to 6:1  1:64 to 2:1  1:24to 1:3  Compound 47 dimethenamid 1:384 to 3:1  1:128 to 1:1  1:48 to1:6  Compound 47 dithiopyr 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3 Compound 47 diuron 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47EPTC 1:768 to 2:1  1:256 to 1:2  1:96 to 1:11 Compound 47 esprocarb1:1371 to 1:2   1:457 to 1:4  1:171 to 1:20  Compound 47 ethalfluralin1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47 ethametsulfuron1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound 47 ethoxyfen  1:8 to 135:1 1:2 to 45:1 1:1 to 9:1 Compound 47 ethoxysulfuron 1:20 to 56:1  1:6 to19:1 1:2 to 4:1 Compound 47 etobenzanid 1:257 to 5:1  1:85 to 2:1  1:32to 1:4  Compound 47 fenoxaprop 1:120 to 10:1  1:40 to 4:1  1:15 to 1:2 Compound 47 fenoxasulfone 1:85 to 14:1 1:28 to 5:1  1:10 to 1:2 Compound 47 fentrazamide 1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound47 flazasulfuron 1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound 47florasulam  1:2 to 420:1  1:1 to 140:1  2:1 to 27:1 Compound 47fluazifop 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3  Compound 47flucarbazone  1:8 to 135:1  1:2 to 45:1 1:1 to 9:1 Compound 47flucetosulfuron  1:8 to 135:1  1:2 to 45:1 1:1 to 9:1 Compound 47flufenacet 1:257 to 5:1  1:85 to 2:1  1:32 to 1:4  Compound 47flumetsulam 1:24 to 48:1  1:8 to 16:1 1:3 to 3:1 Compound 47 flumiclorac 1:10 to 112:1  1:3 to 38:1 1:1 to 7:1 Compound 47 flumioxazin 1:25 to45:1  1:8 to 15:1 1:3 to 3:1 Compound 47 fluometuron 1:384 to 3:1  1:128to 1:1  1:48 to 1:6  Compound 47 flupyrsulfuron  1:3 to 336:1  1:1 to112:1  2:1 to 21:1 Compound 47 fluridone 1:384 to 3:1  1:128 to 1:1 1:48 to 1:6  Compound 47 fluroxypyr 1:96 to 12:1 1:32 to 4:1  1:12 to1:2  Compound 47 flurtamone 1:857 to 2:1  1:285 to 1:3  1:107 to 1:12 Compound 47 fomesafen 1:96 to 12:1 1:32 to 4:1  1:12 to 1:2  Compound 47foramsulfuron 1:13 to 84:1  1:4 to 28:1 1:1 to 6:1 Compound 47glufosinate 1:288 to 4:1  1:96 to 2:1  1:36 to 1:4  Compound 47glyphosate 1:288 to 4:1  1:96 to 2:1  1:36 to 1:4  Compound 47halosulfuron 1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound 47 haloxyfop1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 47 hexazinone 1:192 to6:1  1:64 to 2:1  1:24 to 1:3  Compound 47 imazamox 1:13 to 84:1  1:4 to28:1 1:1 to 6:1 Compound 47 imazapic 1:20 to 56:1  1:6 to 19:1 1:2 to4:1 Compound 47 imazapyr 1:85 to 14:1 1:28 to 5:1  1:10 to 1:2  Compound47 imazaquin 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 47imazethabenz 1:171 to 7:1  1:57 to 3:1  1:21 to 1:3  Compound 47imazethapyr 1:24 to 48:1  1:8 to 16:1 1:3 to 3:1 Compound 47imazosulfuron 1:27 to 42:1  1:9 to 14:1 1:3 to 3:1 Compound 47 indanofan1:342 to 4:1  1:114 to 2:1  1:42 to 1:5  Compound 47 indaziflam 1:25 to45:1  1:8 to 15:1 1:3 to 3:1 Compound 47 iodosulfuron  1:3 to 336:1  1:1to 112:1  2:1 to 21:1 Compound 47 ioxynil 1:192 to 6:1  1:64 to 2:1 1:24 to 1:3  Compound 47 ipfencarbazone 1:85 to 14:1 1:28 to 5:1  1:10to 1:2  Compound 47 isoproturon 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6 Compound 47 isoxaben 1:288 to 4:1  1:96 to 2:1  1:36 to 1:4  Compound 47isoxaflutole 1:60 to 20:1 1:20 to 7:1  1:7 to 2:1 Compound 47 lactofen1:42 to 27:1 1:14 to 9:1  1:5 to 2:1 Compound 47 lenacil 1:384 to 3:1 1:128 to 1:1  1:48 to 1:6  Compound 47 linuron 1:384 to 3:1  1:128 to1:1  1:48 to 1:6  Compound 47 MCPA 1:192 to 6:1  1:64 to 2:1  1:24 to1:3  Compound 47 MCPB 1:288 to 4:1  1:96 to 2:1  1:36 to 1:4  Compound47 mecoprop 1:768 to 2:1  1:256 to 1:2  1:96 to 1:11 Compound 47mefenacet 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47mefluidide 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3  Compound 47mesosulfuron  1:5 to 224:1  1:1 to 75:1  1:1 to 14:1 Compound 47mesotrione 1:42 to 27:1 1:14 to 9:1  1:5 to 2:1 Compound 47 metamifop1:42 to 27:1 1:14 to 9:1  1:5 to 2:1 Compound 47 metazachlor 1:384 to3:1  1:128 to 1:1  1:48 to 1:6  Compound 47 metazosulfuron 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 methabenzthiazuron 1:768 to 2:1 1:256 to 1:2  1:96 to 1:11 Compound 47 metolachlor 1:768 to 2:1  1:256to 1:2  1:96 to 1:11 Compound 47 metosulam  1:8 to 135:1  1:2 to 45:11:1 to 9:1 Compound 47 metribuzin 1:192 to 6:1  1:64 to 2:1  1:24 to1:3  Compound 47 metsulfuron  1:2 to 560:1  1:1 to 187:1  3:1 to 35:1Compound 47 molinate 1:1028 to 2:1   1:342 to 1:3  1:128 to 1:15 Compound 47 napropamide 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6 Compound 47 naptalam 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3  Compound 47nicosulfuron 1:12 to 96:1  1:4 to 32:1 1:1 to 6:1 Compound 47norflurazon 1:1152 to 1:1   1:384 to 1:3  1:144 to 1:16  Compound 47orbencarb 1:1371 to 1:2   1:457 to 1:4  1:171 to 1:20  Compound 47orthosulfamuron 1:20 to 56:1  1:6 to 19:1 1:2 to 4:1 Compound 47oryzalin 1:514 to 3:1  1:171 to 1:2  1:64 to 1:8  Compound 47 oxadiargyl1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47 oxadiazon 1:548 to3:1  1:182 to 1:2  1:68 to 1:8  Compound 47 oxasulfuron 1:27 to 42:1 1:9 to 14:1 1:3 to 3:1 Compound 47 oxaziclomefone 1:42 to 27:1 1:14 to9:1  1:5 to 2:1 Compound 47 oxyfluorfen 1:384 to 3:1  1:128 to 1:1  1:48to 1:6  Compound 47 paraquat 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3 Compound 47 pendimethalin 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6 Compound 47 penoxsulam  1:10 to 112:1  1:3 to 38:1 1:1 to 7:1 Compound47 penthoxamid 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47pentoxazone 1:102 to 12:1  1:34 to 4:1  1:12 to 1:2  Compound 47phenmedipham 1:102 to 12:1  1:34 to 4:1  1:12 to 1:2  Compound 47picloram 1:96 to 12:1 1:32 to 4:1  1:12 to 1:2  Compound 47 picolinafen1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound 47 pinoxaden 1:25 to 45:1 1:8 to 15:1 1:3 to 3:1 Compound 47 pretilachlor 1:192 to 6:1  1:64 to2:1  1:24 to 1:3  Compound 47 primisulfuron  1:8 to 135:1  1:2 to 45:11:1 to 9:1 Compound 47 prodiamine 1:384 to 3:1  1:128 to 1:1  1:48 to1:6  Compound 47 profoxydim 1:42 to 27:1 1:14 to 9:1  1:5 to 2:1Compound 47 prometryn 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound47 propachlor 1:1152 to 1:1   1:384 to 1:3  1:144 to 1:16  Compound 47propanil 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47propaquizafop 1:48 to 24:1 1:16 to 8:1  1:6 to 2:1 Compound 47propoxycarbazone 1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound 47propyrisulfuron 1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound 47propyzamide 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47prosulfocarb 1:1200 to 1:2   1:400 to 1:4  1:150 to 1:17  Compound 47prosulfuron  1:6 to 168:1  1:2 to 56:1  1:1 to 11:1 Compound 47pyraclonil 1:42 to 27:1 1:14 to 9:1  1:5 to 2:1 Compound 47 pyraflufen 1:5 to 224:1  1:1 to 75:1  1:1 to 14:1 Compound 47 pyrasulfotole 1:13to 84:1  1:4 to 28:1 1:1 to 6:1 Compound 47 pyrazolynate 1:857 to 2:1 1:285 to 1:3  1:107 to 1:12  Compound 47 pyrazosulfuron  1:10 to 112:1 1:3 to 38:1 1:1 to 7:1 Compound 47 pyrazoxyfen  1:5 to 224:1  1:1 to75:1  1:1 to 14:1 Compound 47 pyribenzoxim  1:10 to 112:1  1:3 to 38:11:1 to 7:1 Compound 47 pyributicarb 1:384 to 3:1  1:128 to 1:1  1:48 to1:6  Compound 47 pyridate 1:288 to 4:1  1:96 to 2:1  1:36 to 1:4 Compound 47 pyriftalid  1:10 to 112:1  1:3 to 38:1 1:1 to 7:1 Compound47 pyriminobac 1:20 to 56:1  1:6 to 19:1 1:2 to 4:1 Compound 47pyrimisulfan 1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound 47pyrithiobac 1:24 to 48:1  1:8 to 16:1 1:3 to 3:1 Compound 47pyroxasulfone 1:85 to 14:1 1:28 to 5:1  1:10 to 1:2  Compound 47pyroxsulam  1:5 to 224:1  1:1 to 75:1  1:1 to 14:1 Compound 47quinclorac 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3  Compound 47quizalofop 1:42 to 27:1 1:14 to 9:1  1:5 to 2:1 Compound 47 rimsulfuron1:13 to 84:1  1:4 to 28:1 1:1 to 6:1 Compound 47 saflufenacil 1:25 to45:1  1:8 to 15:1 1:3 to 3:1 Compound 47 sethoxydim 1:96 to 12:1 1:32 to4:1  1:12 to 1:2  Compound 47 simazine 1:384 to 3:1  1:128 to 1:1  1:48to 1:6  Compound 47 sulcotrione 1:120 to 10:1  1:40 to 4:1  1:15 to 1:2 Compound 47 sulfentrazone 1:147 to 8:1  1:49 to 3:1  1:18 to 1:3 Compound 47 sulfometuron 1:34 to 34:1 1:11 to 12:1 1:4 to 3:1 Compound47 sulfosulfuron  1:8 to 135:1  1:2 to 45:1 1:1 to 9:1 Compound 47tebuthiuron 1:384 to 3:1  1:128 to 1:1  1:48 to 1:6  Compound 47tefuryltrione 1:42 to 27:1 1:14 to 9:1  1:5 to 2:1 Compound 47tembotrione 1:31 to 37:1 1:10 to 13:1 1:3 to 3:1 Compound 47tepraloxydim 1:25 to 45:1  1:8 to 15:1 1:3 to 3:1 Compound 47 terbacil1:288 to 4:1  1:96 to 2:1  1:36 to 1:4  Compound 47 terbuthylatrazine1:857 to 2:1  1:285 to 1:3  1:107 to 1:12  Compound 47 terbutryn 1:192to 6:1  1:64 to 2:1  1:24 to 1:3  Compound 47 thenylchlor 1:85 to 14:11:28 to 5:1  1:10 to 1:2  Compound 47 thiazopyr 1:384 to 3:1  1:128 to1:1  1:48 to 1:6  Compound 47 thiencarbazone  1:3 to 336:1  1:1 to 112:1 2:1 to 21:1 Compound 47 thifensulfuron  1:5 to 224:1  1:1 to 75:1  1:1to 14:1 Compound 47 thiobencarb 1:768 to 2:1  1:256 to 1:2  1:96 to 1:11Compound 47 topramazone  1:6 to 168:1  1:2 to 56:1  1:1 to 11:1 Compound47 tralkoxydim 1:68 to 17:1 1:22 to 6:1  1:8 to 2:1 Compound 47triallate 1:768 to 2:1  1:256 to 1:2  1:96 to 1:11 Compound 47triasulfuron  1:5 to 224:1  1:1 to 75:1  1:1 to 14:1 Compound 47triaziflam 1:171 to 7:1  1:57 to 3:1  1:21 to 1:3  Compound 47tribenuron  1:3 to 336:1  1:1 to 112:1  2:1 to 21:1 Compound 47triclopyr 1:192 to 6:1  1:64 to 2:1  1:24 to 1:3  Compound 47trifloxysulfuron  1:2 to 420:1  1:1 to 140:1  2:1 to 27:1 Compound 47trifluralin 1:288 to 4:1  1:96 to 2:1  1:36 to 1:4  Compound 47triflusulfuron 1:17 to 68:1  1:5 to 23:1 1:2 to 5:1 Compound 47tritosulfuron 1:13 to 84:1  1:4 to 28:1 1:1 to 6:1

The present disclosure also includes Tables A2 through A22 which areeach constructed the same as Table A1 above except that entries belowthe “Component (a)” column heading are replaced with the respectiveComponent (a) Column Entry shown below. Thus, for example, in Table A2the entries below the “Component (a)” column heading all recite“Compound 50”, and the first line below the column headings in Table A2specifically discloses a mixture of Compound 50 with 2,4-D. Tables A3through A22 are constructed similarly.

Table Number Component (a) Column Entries A2  Compound 50  A3  Compound52  A4  Compound 59  A5  Compound 75  A6  Compound 81  A7  Compound 82 A8  Compound 83  A9  Compound 85  A10 Compound 87  A11 Compound 96  A12Compound 97  A13 Compound 107 A14 Compound 118 A15 Compound 128 A16Compound 133 A17 Compound 169 A18 Compound 175 A19 Compound 186 A20Compound 218 A21 Compound 240 A22 Compound 243

The following Tests demonstrate the herbicidal effect of the compoundsof this invention against specific weeds. The weed control afforded bythe compounds is not limited, however, to the plant species tested. SeeIndex Tables A-I for compound descriptions. The following abbreviationsare used in the Index Tables which follow: “Cmpd” means Compound, Me ismethyl, Et is ethyl, c-Pr is cyclopropyl, i-Bu is isobutyl (i.e.—CH₂CH(CH₃)₂), Ph is phenyl, OMe is methoxy, c-hex is cyclohexyl, n-hexis normal hexyl Bn in benzyl, acetylene means —C≡CH, and SMe ismethylthio. The abbreviation “Ex.” stands for “Example” and is followedby a number indicating in which example the compound is prepared.Substitution is noted in parenthases following the listed ring, forexample Ph(4-OMe) indicates that the phenyl group is substituted bymethoxy at the 4-position (relative to the point of attachment of thephenyl group to the remainder of the Formula 1 compound).

INDEX TABLE A

Cmpd R¹ R² R³ m.p. (° C.)  1 CH₃ c-Pr OH * 2 (Ex. 1) Ph Ph OH * **  3 Etc-Pr OH *  4 Ph(4-OMe) Ph OH *  7 Ph Et OH *  8 Ph(4-Me) Ph OH *  9Ph(3-Cl) Ph OH 101-102  10 Ph(2-Cl) Ph OH 142-143  11 Ph(4-Cl) Ph OH83-85  12 Ph(2-Me) Ph OH 181-182  13 Ph(4-Cl) Ph O⁻K⁺ 105-108  14 Ph PhO⁻K⁺ 128-130  15 Ph(2-OMe) Ph OH 178-179 17 (Ex. 2) —CH₂Ph Ph OH   57-58**  18 Ph(3-Me) Ph OH 77-78  19 Ph(3-OMe) Ph OH 87-88  22 Ph(3-F) Ph OH72-74  23 —CH₂CH═CH₂ Ph OH 38-40  24 Ph(4-F) Ph OH 131-132  25 PhPh(4-Cl) OH *  26 Ph(2-F) Ph OH 142-144  27 Ph(2,3-di-Me) Ph OH 155-157 28 Ph(2,4-di-Me) Ph OH 186-187  29 Ph(2,5-di-Me) Ph OH 169-171  30 PhSMe OH 92-94  31 Ph(2,6-di-Me) Ph OH 177-178  32 Ph(3,4-di-Me) Ph OH165-166  33 Ph(3,5-di-Me) Ph OH 156-157  34 Ph Ph(3-Cl) OH 131-135  35Ph Ph(2-Cl) OH 138-142  36 Ph(2-Me) Ph(3-Cl) OH 82-83  37 Ph(2-Br) Ph OH170-171  38 Ph(3-Br) Ph OH 105-107  39 Ph(4-Me) Ph(3-Cl) OH 78-80  40Ph(3-Cl-2-Me) Ph OH 170-171  41 Ph(2-Cl-4-Me) Ph OH 183-184  42 Ph n-BuOH 145-147  43 Ph(4-Cl-2-Me) Ph OH 172-173  44 Ph(5-F-2-Me) Ph OH169-170  45 Ph(3-Me) Ph(3-Cl) OH 69-70  46 Ph(2-Cl-6-Me) Ph OH 180-18147 (Ex. 5) Ph(3-F-2-Me) Ph OH 168-169  48 Ph(4-F-2-Me) Ph OH 153-155  49Et Ph OH 62-66  50 n-Pr Ph OH 106-108  51 Ph(2-F-5-Me) Ph OH 159-161  52Ph(5-Cl-2-Me) Ph OH 165-166  53 Ph(4-F-3-Me) Ph OH 152-153  54 Ph n-hexOH 138-140  55 Me Ph OH 152-154  56 Ph 3-thienyl OH *  57 Ph(2,4-di-F)Ph OH 153-154  58 Ph(2-F,3-Me) Ph OH 161-162  59—CH₂(tetrahydrofuran-2yl) Ph OH 155-156  60 Ph i-Pr OH *  61 —CH₂C≡CH Ph151-153  62 Ph(2-Me) n-Bu OH 100-101  63 Ph(3-Me) n-Bu OH 136-137  64Ph(4-Cl) Ph(3-Cl) OH 140-142  65 Ph 2-thienyl(5-Cl) OH *  66 Ph2-thienyl OH *  67 Ph(4-Me) n-Bu OH 143-144  68 Ph i-Bu OH *  69 PhPh(3-Br) OH *  70 Ph Ph(4-Br) OH *  71 Ph Ph(2-Br) OH *  72 n-Pr n-Pr OH95-97  73 Ph(2-Me) n-Pr OH 127-128  74 —CH₂(tetrahydrofuran-2-yl) n-PrOH 95-96  75 n-Bu n-Pr OH 88-89  76 Ph furan-2-yl OH *  77 n-Pr2-thienyl OH *  78 Ph n-pentyl OH *  79 Ph(3-Me) n-Pr OH 140-142  80 PhPh(4-Me) OH 164-169  81 —CH₂CH₂CH₂OCH₃ Ph OH 121-122  82 Ph Ph(2-Me) OH165-167  83 Ph Ph OC(═O)—i-Bu 175-176  84 —CH₂(Ph(3,4-di-OMe)) n-Pr OH * 85 —CH₂CH₂OCH₃ Ph OH 135-137  86 n-Bu Ph OH *  87 Ph c-Pr OH *  88 PhPh OC(═O)—c-Pr 167-168  89 n-pentyl Ph OH 100-102  90 c-Pr Ph OH 172-174 91 —CH₂CH₂OCH₂CH₂OCH₃ Ph OH 138-139  92 Ph c-pentyl OH *  93 n-Pr3-thienyl OH *  94 n-hex Ph OH 95-97  95 i-Pr Ph OH 163-165  96—CH₂CH₂OCH₂CH₃ Ph OH 129-131 97 (Ex. 10) —CH₂CH₂OCH₃ 3-thienyl OH103-105  98 —CH₂(tetrahydrofuran-2-yl) 3-thienyl OH *  99 c-hex3-thienyl OH * 100 n-Pr Ph(3-OMe) OH * 101 n-Pr Ph(2-F) OH 136-138 102n-Pr Ph(4-F) OH 100-103 103 Bn n-Pr OH * 104 —CH₂(Ph(3-OMe)) n-Pr OH *105 —CH₂(Ph(3-OCF₃)) n-Pr OH * 106 Ph c-hex OH * 107 —CH(CH₃)CH₂OCH₃ PhOH 122-123 108 —CH₂CH₂OCH₃ 2-thienyl OH * 109 —CH₂(tetrahydrofuran-2-yl)2-thienyl OH * 110 n-Pr furan-2-yl OH * 111 —CH₂CH₂OCH₃ furan-2-yl OH *112 n-Pr Ph(4-OMe) OH * 113 (Ex. 7) Ph 3-pyridinyl OH ** 114 Ph c-BuOH * 115 Et Ph(3-Me) OH * 116 n-Bu Ph(3-Me) OH * 117 —CH₂CH₂OCH₃Ph(3-Me) OH * 118 —CH₂CH₂CH₂OCH₃ Ph(3-Me) OH * 119 —CH₂CH₂OCH₃Ph(3,5-di-F) OH 154-178 120 —CH₂CH₂CH₂OCH₃ Ph(3,5-di-F) OH 139-140 121n-Bu Ph(3,5-di-F) OH 144-145 122 Et Ph(3,5-di-F) OH 162-165 123—CH₂CH₂OCH₃ Ph(3-F) OH * 124 Et Ph(3-F) OH * 125 n-Bu Ph(3-F) OH * 126—CH₂CH₂CH₂OCH₃ Ph(3-F) OH * 127 n-Pr Ph(3-F) OH * 128 (Ex. 11) c-hex PhOH 160-163 ** 129 tetrahydropyran-4-yl Ph OH * 130 c-heptyl Ph OH * 131c-pentyl Ph OH * 132 Ph(4-F-3-Me) Ph(3-Br) OH * 133 Ph(4-F-3-Me)Ph(3-Cl) OH * 134 n-Pr Ph(4-Br) OH * 135 n-Pr 1-Me-pyrazol-3-yl OH * 136—CH₂CH₂OCH₃ 1-Me-pyrazol-3-yl OH * 137 Et Ph(3-Br) OH 141-145 138 n-BuPh(3-Br) OH 112-113 139 —CH₂CH₂OCH₃ Ph(3-Br) OH 115-116 140—CH₂CH₂CH₂OCH₃ Ph(3-Br) OH 118-119 141 n-Pr Ph(3-Br) OH 134-137 142—CH₂(tetrahydrofuran-2-yl) Ph(3-Cl) OH * 143 —CH₂CH₂CH₂OCH₃ Ph(3-Cl)OH * 144 Ph(5-Cl-2-Me) Ph(3-Br) OH * 145 Et Ph(3-Cl) OH 114-115 146 n-BuPh(3-Cl) OH 104-112 147 —CH₂CH₂OCH₃ Ph(3-Cl) OH 124-125 148Ph(5-Cl-2-Me) Ph(3-Cl) OH * 149 n-Pr 1,4-benzodioxan-6- OH * yl 150 n-Prnaphthalen-2-yl OH * 151 Ph(4-OMe) Ph(3-Cl) OH 154-156 152 n-PrPh(3,5-di-F) OH * 153 n-Pr c-Pr OH 163-165 154 Ph(5-F-2-Me) Ph(3-Br)OH * 155 n-Pr Ph(3-CF₃) OH 129-131 156 n-Pr Ph(3,5-di-Me) OH 161-163 157Ph(5-F-2-Me) Ph(3-Cl) OH * 158 Ph(4-Et) Ph(3,5-di-F) OH 181-182 159Ph(2-Me) Ph(3,5-di-F) OH 166-168 160 c-hex c-Pr OH 173-175 161 PhPh(3,5-di-F) OH 147-148 162 Ph(4-Me) Ph(3,5-di-F) OH 191-192 163—CH₂—c-hex Ph(3,5-di-F) OH * 164 tetrahydrothiopyran-4-yl Ph OH * 165c-dodecahexyl Ph OH * 166 Ph(4-F-2-Me) Ph(3-Br) OH * 167 Ph(4-F-2-Me)Ph(3-Cl) OH * 168 (Ex. 8) (cis/trans)-tetrahydro-1-oxido-2H- Ph OH **thiopyran-4-yl 169 (Ex. 8) (trans/cis)-tetrahydro-1-oxido-2H- Ph OH **thiopyran-4-yl 170 —CH₂C≡CH Ph(3,5-di-F) OH * 171 —CH₂CH₂OCH₂CH₂OCH₃Ph(3,5-di-F) OH * 172 n-Pr Ph(3-Me) OH 116-117 173 n-Pr Ph(3,5-di-Cl) OH 97-100 174 Ph(4-Et) Ph(3-Cl) OH 146-148 175 Ph(4-Et) Ph(3-Br) OH126-129 176 Ph(4-OMe) Ph(3-Br) OH 120-124 177 Ph(4-Et) Ph(3-Br) OH139-142 178 Ph(5-F-2-Me) Ph(3-Me) OH * 179 Ph(5-Cl-2-Me) Ph(3,5-di-F)OH * 180 —CH₂(tetrahydrofuran-2-yl) Ph(3,5-di-F) OH * 181 c-hexPh(3,5-di-F) OH * 182 —CH₂CH₂OCH₂CH₃ Ph(3,5-di-F) OH * 183 Ph(5-F-2-Me)Ph(3,5-di-F) OH * 184 Ph(5-Cl-2-Me) Ph(3-F) OH * 185 c-hex Ph(3-Me) OH *186 tetrahydropyran-4-yl 3-thienyl OH * 187 c-hex Ph(3-F) OH * 188 c-hexfuran-2-yl OH * 189 c-hex 2-thienyl OH * 190 n-Pr Ph(3-Cl) OH 123-125191 Ph(4-F-3-Me) Ph(3-F) OH * 192 Ph(4-F-2-Me) Ph(3-Me) OH * 193 n-Buc-Pr OH 140-142 194 c-hex Ph(3-Et) OH * 195 c-hex Ph(3-CF₃) OH * 196c-hex Ph(3-OMe) OH * 197 c-hex Ph(4-F) OH * 198 c-hex Ph(3,4-di-F) OH *199 Ph Ph(3-F) OH * 200 Et Bn OH * 201 Ph(2-Me) Ph(3-F) OH * 202Ph(4-Me) Ph(3-F) OH * 203 Ph(4-OMe) Ph(3-F) OH * 204 Ph(4-Et) Ph(3-F)OH * 205 c-hex Ph(3,4,5-tri-F) OH * 206 c-hex Ph(3-Br) OH * 207—CH₂CH₂CF₃ Ph OH * 208 —CH₂CH₂CF₃ Ph(3-F) OH 69-70 209 Ph(2-Me) Ph(3-Br)OH 144-146 210 Ph(2-Me) Ph(3-Me) OH 152-154 211 Ph(4-Me) Ph(3-Me) OH146-148 212 Ph(4-OMe) Ph(3-Me) OH 156-158 213 Ph(4-Et) Ph(3-Me) OH147-148 214 —CH₂CH₂CHCH₂ Ph OH 124-127 215 c-octyl Ph OH 216 c-hexPh(4-acetylene) OH * 217 Ph n-Pr OH 145-147 218 Ph(3,4-di-OMe) Ph OH164-165 219 Ph(4-Et) Ph OH 160-162 220 Ph(3-Et) Ph OH 126-127 255Ph(2-Et) Ph OH 171-172 256 Ph(2,4-diOMe) Ph OH 182-183 257—CH₂CH₂CH₂CH₂CH₂— OH * * See Index Table J for M.S. or ¹H NMR data. **See synthesis examples for ¹H NMR data.

INDEX TABLE B

Cmpd R¹ R² R³ m.p. (° C.)  16 Ph Ph OS(O)₂Ph(4-Me) 63-65    20 (Ex. 3)—CH₂Ph Ph OH 56-57 ** 21 (Ex. 4) —CH₂Ph Ph OS(O)₂Ph(4-Me) 52-53 ** 221n-Pr 2-thienyl OH * * See Index Table J for M.S. or ¹H NMR data. ** Seesynthesis example for ¹H NMR data.

INDEX TABLE C

Cmpd R¹ R² m.p. (° C.) 222 Ph(2,5-di-Me) Ph * 223 (Ex. 6) Ph Ph ** * SeeIndex Table J for M.S. or ¹H NMR data. ** See synthesis examples for ¹HNMR data.

INDEX TABLE D

Cmpd R¹ R² R³ m.p. (° C.) 224 n-Pr Ph(3,5-di-F) OH * 225 Ph Ph OH125-127 * See Index Table J for M.S. or ¹H NMR data.

INDEX TABLE E

Cmpd R¹ R² R³ m.p. (° C.) 226 n-Pr Ph OH * 227 n-Pr 3-thienyl OH * 228—CH₂CH₂OCH₃ 3-thienyl OH * 229 —CH₂(tetrahydrofuran- 3-thienyl OH *2-yl) 230 n-Pr furan-2-yl OH * 231 Et Ph(3-Me) OH * 232 n-Bu Ph(3-Me)OH * 233 —CH₂CH₂OCH₃ Ph(3-Me) OH * 234 Ph(3-F-2-Me) Ph OH * 235—CH₂CH₂OCH₃ Ph(3-F) OH * 236 Et Ph(3-F) OH * 237 n-Bu Ph(3-F) OH * 238—CH₂CH₂CH₂OCH₃ Ph(3-F) OH * 239 Et Ph OH * 240 n-Bu Ph OH * 241 n-Pr1,4-benzodioxan- OH * 6-yl 242 n-Pr naphthalen-2-yl OH * 243 (Ex. 9)—CH₂CH₂OCH₃ Ph(3,5-di-F) OH ** 244 —CH₂CH₂CH₂OCH₃ Ph(3,5-di-F) OH * 245n-Bu Ph(3,5-di-F) OH * 246 Ph Ph(3,5-di-F) OH 158-159 247 c-dodecahexylPh OH * 248 c-hex Ph OH * 249 tetrahydropyran-4-yl Ph OH * 250—CH₂(tetrahydrofuran- Ph OH * 2-yl) 251 c-hex Ph(3,4,5-tri-F) OH * 252c-hex Ph(3-Br) OH * 253 c-heptyl Ph OH * 254 c-hex Ph(4-acetylene)OH * * See index table J for ¹H NMR. ** See synthesis example for ¹H NMRdata.

INDEX TABLE F

Cmpd R¹ R² m.p. (° C.) 2Q (Ex. 1) Ph Ph ** 17Q (Ex. 2) —CH₂Ph Ph **  23Q—CH₂CH═CH₂ Ph * 47Q (Ex. 5) Ph(3-F-2-Me) Ph **  59Q—CH₂(tetrahydrofuran-2yl) Ph *  61Q —CH₂C≡CH Ph *  76Q Ph 2-furanyl * 84Q —CH₂(Ph(3,4-di-OMe)) n-Pr * 105Q —CH₂(Ph(3-OCF₃)) n-Pr * 113Q (Ex.7) Ph 3-pyridinyl ** 153Q n-Pr c-Pr * 163Q —CH₂—c-hex Ph(3,5-di-F) *212Q Ph(4-OMe) Ph(3-Me) * 257Q —CH₂CH₂CH₂CH₂CH₂— * * See Index Table Jfor MS or ¹H NMR data. ** See synthesis examples for ¹H NMR data.

INDEX TABLE G

Cmpd R¹ R² m.p. (° C.) 20Q (Ex. 3) —CH₂Ph Ph ** ** See synthesis examplefor ¹H NMR data.

INDEX TABLE H

m.p. Cmpd R¹ R² (° C.) 2R (Ex. 1) Ph Ph ** 17R (Ex. 2) —CH₂Ph Ph **  23R—CH₂CH═CH₂ Ph * 47R (Ex. 5) Ph(3-F-2-Me) Ph **  59R—CH₂(tetrahydrofuran-2-yl) Ph *  61R —CH₂C≡CH Ph *  76R Ph 2-furanyl * 84R —CH₂(Ph(3,4-di-OMe)) n-Pr * 105R —CH₂(Ph(3-OCF₃)) n-Pr * 97R (Ex.10) —CH₂CH₂OCH₃ 3-thienyl ** 118R —CH₂CH₂CH₂OCH₃ Ph(3-Me) * 113R (Ex. 7)Ph 3-pyridinyl ** 135R n-Pr 1-Me-pyrazol-3-yl * 128R (Ex. 11) c-hex Ph** 153R n-Pr c-Pr * 163R —CH₂—c-hex Ph(3,5-di-F) * 164Rtetrahydrothiopyran-4-yl Ph * 186R tetrahydropyran-4-yl 3-thienyl * 212RPh(4-OMe) Ph(3-Me) * 216R c-hex Ph(4-acetylene) * 242R n-Prnaphthalene-2-yl * 247R c-dodecahexyl Ph * 243R (Ex. 9) —CH₂CH₂OCH₃Ph(3,5-di-F) ** 257R —CH₂CH₂CH₂CH₂CH₂— * * See Index Table J for MS or¹H NMR data. ** See synthesis examples for ¹H NMR data.

INDEX TABLE I

m.p. Cmpd R¹ R² R²³ (° C.) 2S (Ex. 1) Ph Ph Et ** 17S (Ex. 2) —CH₂Ph PhEt **  23S —CH₂CH═CH₂ Ph Et *  59S —CH₂(tetrahydrofuran- Ph Et * 2-yl) 61S —CH₂C≡CH Ph Et *  84S —CH₂(Ph(3,4-di-OMe)) n-Pr Et * 105S—CH₂(Ph(3-OCF₃)) n-Pr Et * 97S (Ex. 10) —CH₂CH₂OCH₃ 3-thienyl Et ** 118S—CH₂CH₂CH₂OCH₃ Ph(3-Me) Et * 113S (Ex. 7) Ph 3-pyridinyl Et ** 135S n-Pr1-Me-pyrazol- Et * 3-yl 128S (Ex. 11) c-hex Ph Et ** 153S n-Pr c-Pr Me *163S —CH₂—c-hex Ph(3,5-di-F) Et * 164S tetrahydrothiopyran-4-yl Ph Et *186S tetrahydropyran-4-yl 3-thienyl Et * 212S Ph(4-OMe) Ph(3-Me) Et *216S c-hex Ph(4-acetylene) Et * 242S n-Pr naphthalene-2-yl Et * 247Sc-dodecahexyl Ph Et * 243S (Ex. 9) —CH₂CH₂OCH₃ Ph(3,5-di-F) Et ** 257S—CH₂CH₂CH₂CH₂CH₂— Et * * See Index Table J for MS or ¹H NMR data. ** Seesynthesis examples for ¹H NMR data.

INDEX TABLE J Cmpd Mass spectra data^(a) or ¹H NMR data^(b) 1 289 3 3034 417 7 339 8 401 25 421 56 393 60 353 (ESI, M + 1) 65 427 66 393 68 367(ESI, M + 1) 69 (500 MHz) δ 16.38 (s, 1H), 8.14 (s, 1H), 7.45 (t, 1H),7.34 (dd, 1H), 7.32-7.23 (m, 3H), 7.10-7.05 (m, 3H), 7.01-6.95 (m, 1H),2.64 (t, 2H), 2.40 (t, 2H), 1.96 (dd, 2H). 70 465 71 463 (AP, M − H) 76377 77 359 78 381 (ESI, M + H) 84 425 (AP, M − H) 86 367 87 351 (ESI,M + H) 92 379 (ESI, M + H) 93 359 98 401 99 399 100 381 (EST, M − H) 103δ 16.41 (s, 1H), 8.09 (s, 1H), 7.42 (m, 3H), 7.21 (m, 2H), 5.29 (s, 2H),2.79 (m, 2H), 2.77 (m, 2H), 2.65 (m, 2H), 2.15 (m, 2H), 1.75 (m, 2H),0.94 (t, 3H). 104 δ 16.22 (s, 1H), 8.07 (s, 1H), 7.25 (m, 1H), 6.77 (m,3H), 5.29 (s, 2H), 3.81 (s, 3H), 2.79 (m, 2H), 2.64 (m, 2H), 2.55 (m,2H), 2.15 (m, 2H), 1.65 (m, 2H), 0.95 (t, 3H). 105 δ 16.41 (s, 1H), 8.06(s, 1H), 7.41 (m, 1H), 7.14 (m, 3H), 5.32 (s, 2H), 2.81 (m, 2H), 2.62(m, 2H), 2.52 (m, 2H), 2.15 (m, 2H), 1.81 (m, 2H), 0.95 (t, 3H). 106 393(ESI, M + H) 108 375 109 401 110 343 111 359 112 382 114 365 (ESI, M +H) 115 353 116 381 117 383 118 397 123 387 124 357 125 385 126 401 127 δ8.09 (s, 1H), 7.55-7.46 (m, 1H), 7.33-7.20 (m, 3H), 3.94-3.83 (m, 2H),2.74 (t, 2H), 2.51 (t, 2H), 2.08 (quin, 2H), 1.63 (sxt, 2H), 0.78 (t,3H). 129 395 130 407 131 379 132 495 (AP, M − H) 133 453 134 431 (ESI,M + H) 135 357 136 373 142 429 143 417 144 (500 MHz) δ 16.32 (br s, 1H),8.22 (s, 1H), 7.55 (s, 1H), 7.46 (d, 1H), 7.25-7.06 (m, 5H), 2.70 (br s,2H), 2.46 (d, 2H), 2.14 (s, 3H), 2.08-2.00 (m, 2H) 148 469 149 411 150403 152 389 154 497 157 453 163 443 164 411 165 477 166 495 (AP, M − H)167 453 170 385 171 449 178 433 179 471 180 431 181 429 182 419 183 455184 453 185 δ 16.65 (br s, 1H), 8.00 (s, 1H), 7.20-7.40 (m, 4H),3.90-4.00 (m, 1H), 0.90-2.80 (m, 19H). 186 401 187 411 188 383 189 399191 437 192 433 194 421 195 461 196 423 197 411 198 429 199 403 (AP, M −H) 200 353 201 417 (AP, M − H) 202 417 (AP, M − H) 203 433 (AP, M − H)204 431 (AP, M − H) 205 447 206 471 207 405 (AP, M − H) 215 421 216 417221 359 222 412 224 417 226 379 227 385 228 401 229 427 230 369 231 379232 407 233 409 234 445 235 413 236 383 237 411 238 427 239 365 240 393241 437 242 429 244 445 245 429 247 503 248 419 249 421 250 δ 16.75 (d,1H), 8.09 (s, 1H), 7.53 (m, 2H), 7.49 (m, 3H), 4.35 (m, 3H), 3.85 (m,1H), 3.61 (m, 1H), 3.31 (m, 1H), 3.15 (m, 1H), 2.95 (m, 1H), 2.20-1.20(m, 9H). 251 473 252 497 253 433 254 443 257 δ 16.60 (s, 1H), 7.94 (s,1H), 4.32 (m, 2H), 3.02 (m, 2H), 2.74 (m, 2H), 2.45 (m, 2H), 2.06 (m,2H), 1.85 (m, 4H), 1.8 (m, 2H). 23Q δ 8.80 (s, 1H), 7.46-7.66 (m, 5H),6.04 (m, 1H), 5.86-5.98 (m, 1H), 5.26 (m, 1H), 5.02 (m, 1H), 4.62 (m,2H), 2.69 (m, 2H), 2.42 (m, 2H), 2.12 (m, 2H). 59Q δ 8.78 (s, 1H),7.49-7.57 (m, 5H), 6.03 (s, 1H), 4.28-4.39 (m, 2H), 3.94 (m, 1H), 3.59(m, 1H), 3.33 (m, 1H), 2.68 (m, 2H), 2.45 (m, 2H), 2.12 (m, 2H), 1.99(m, 1H), 1.76 (m, 1H), 1.57-1.66 (m, 1H), 1.39 (m, 1H). 61Q δ 8.81 (s,1H), 7.77 (m, 2H), 7.57 (m, 3H), 6.04 (s, 1H), 4.69 (m, 2H), 2.69 (m,2H), 2.46 (m, 3H), 2.12 (m, 2H). 76Q δ 8.91 (s, 1H), 7.60 (m, 3H), 7.56(m, 1H), 7.28 (dd, 2H), 6.35 (dd, 1H), 6.03 (s, 1H), 5.75 (d, 1H), 2.66(t, 2H), 2.44 (m, 2H), 2.09 (m, 2H). 84Q δ 8.71 (s, 1H), 6.80 (m, 2H),6.78 (d, 1H), 6.01 (s, 1H), 5.34 (s, 2H), 3.86 (d, 6H), 2.8 (m, 2H),2.75 (m, 2H), 2.45 (m, 2H), 2.20 (m, 2H), 1.80 (m, 2H), 1.00 (t, 3H).105Q δ 8.74 (s, 1H), 7.40 (m, 1H), 7.20 (m, 1H), 7.15 (m. 1H), 7.00 (s,1H), 6.00 (s, 1H), 5.40 (s, 2H), 2.78 (m, 2H), 2.72 (m, 2H), 2.40 (m,2H), 2.15 (m, 2H), 1.80 (m, 2H), 0.94 (m, 3H). 153Q (300 MHz) δ 8.57 (s,1H), 5.98 (s, 1H), 4.25-4.19 (m, 2H), 2.67-2.63 (m, 2H), 2.45-2.41 (m,2H), 2.13-1.92 (m, 3H), 1.86-1.78 (m, 2H), 1.42-1.37 (m, 2H), 1.26-1.20(m, 2H), 1.07-1.02 (m, 3H). 163Q (500 MHz) δ 8.72 (s, 1H), 7.13-6.95 (m,3H), 6.03 (s, 1H), 3.98 (d, 2H), 2.69 (td, 2H), 2.53-2.39 (m, 2H), 2.12(quin, 2H), 1.75 (ddt, 1H), 1.66-1.57 (m, 3H), 1.50-1.43 (m, 2H),1.19-0.99 (m, 3H), 0.77-0.66 (m, 2H). 212Q δ 8.86 (s., 1H), 7.07-7.32(m, 4H), 6.80-7.06 (m, 4H), 6.04 (s., 1H), 3.78 (s, 3H), 2.67 (m, 2H),2.44 (m, 2H), 2.27 (s, 3H), 2.11 (m, 2H). 257Q δ 8.60 (s, 1H), 6.00 (s,1H), 4.40 (m, 2H), 3.15 (m, 2H), 2.66 (m, 2H), 2.44 (m, 2H), 2.15 (m,2H), 1.85 (m, 6H). 23R δ 9.03 (s, 1H), 7.42-7.76 (m, 5H), 5.82-6.04 (m,1H), 5.42 (m, 1H), 5.04 (m, 1H), 4.72 (m, 2H). 59R δ 9.00 (s, 1H),7.48-7.60 (m, 5H), 4.35 (m, 1H), 4.24-4.32 (m, 1H), 4.06 (m, 1H),3.53-3.65 (m, 1H), 3.29-3.41 (m, 1H), 2.02 (m, 1H), 1.79 (m, 1H),1.57-1.69 (m, 1H), 1.41 (m, 1H). 61R δ 13.02 (br s, 1H), 8.65 (s, 1H),7.73 (m, 2H), 7.62 (m, 3H), 4.58 (m, 2H), 3.44 (m, 1H). 76R δ 12.64 (brs, 1H), 9.11 (s, 1H), 7.66 (m, 3H), 7.56 (d, 1H), 7.33 (m, 2H), 6.39(dd, 1H), 5.93 (d, 1H). 84R δ 13.00 (br s, 1H), 8.92 (s, 1H), 6.80 (d,1H), 6.79 (s, 1H), 6.85 (d, 1H), 5.34 (s, 2H), 3.87 (d, 6H), 2.80 (m,2H), 1.80 (m, 2H), 1.01 (t, 3H). 105R δ 12.8 (br s, 1H), 8.94 (s, 1H),7.45 (m, 1H), 7.25 (m, 1H), 7.15 (m, 1H), 7.05 (s, 1H), 5.41 (s, 2H),2.77 (m, 2H), 1.88 (m, 2H), 0.99 (t, 3H). 118R δ 8.98 (s, 1H), 7.42 (m,2H), 7.33 (m, 2H), 4.26 (m, 2H), 3.31 (t, 3H), 3.16 (s, 3H), 2.45 (s,3H), 1.95 (m, 3H). 135R δ 13.33 (s, 1H), 8.95 (s, 1H), 7.50 (d, 1H),7.11 (d, 1H), 4.69 (m, 2H), 4.04 (s, 3H), 1.86 (m, 2H), 1.01 (t, 3H).153R (300 MHz) δ 13.15 (br s, 1H), 8.76 (s, 1H), 4.31-4.25 (m, 2H),2.04-1.99 (m, 1H), 1.90-1.80 (m, 2H), 1.45-1.41 (m, 2H), 1.31-1.25 (m,2H), 1.09 (t, 3H). 163R (500 MHz) δ 12.77 (br s, 1H), 7.19-6.94 (m, 3H),4.08 (d, 2H), 1.86-1.52 9m, 4H), 1.44 (d, 2H), 1.22-0.95 (m, 3H),0.82-0.63 (m, 2H). 164R δ 13.12 (br s, 1H), 8.95 (s, 1H), 7.59 (m, 3H),7.46 (m, 2H), 4.09 (s, 1H), 3.08 (d, 2H), 2.69 (d, 2H), 2.46 (m, 2H),2.05 (m, 2H). 186R δ 13.12 (br s, 1H), 8.93 (s, 1H), 7.83 (m, 1H), 7.58(m, 1H), 7.29 (m, 1H), 4.56 (m, 1H), 4.09 (m, 2H), 3.26 (m, 2H), 3.12(m, 2H), 1.67 (m, 2H). 212R δ 9.09 (s, 1H), 6.98-7.21 (m, 6H), 6.90 (d,2H), 3.81 (s, 3H), 2.28 (s, 3H). 216R δ 13.25 (br s, 1H), 8.93 (s, 1H),7.67 (m, 2H), 7.48 (m, 2H), 4.06 (m, 1H), 3.28 (s, 1H), 2.68 (dd, 2H),1.85 (d, 2H), 1.73 (d, 2H), 1.63 (m, 1H), 1.24 (m, 1H), 1.05 (m, 2H).242R δ 13.14 (br s, 1H), 9.03 (s, 1H), 8.05 (m, 2H), 7.96 (d, 2H), 7.65(ddd, 2H), 7.56 (dd, 1H), 4.14 (m, 2H), 1.75 (m, 2H), 0.80 (t, 3H). 247Rδ 13.26 (br s, 1H), 8.96 (s, 1H), 7.57 (m, 3H), 7.46 (m, 2H), 4.45 (m,1H), 2.32 (m, 2H), 1.99 (m, 2H), 1.18 (m, 15H), 0.69 (m, 3H). 257R δ13.00 (br s, 1H), 8.75 (s, 1H), 4.42 (m, 2H), 3.10 (m, 2H), 1.82 (m, 6H)23S δ 8.70 (s, 1H), 7.49-7.53 (m, 5H), 5.85-5.97 (m, 1H), 5.25 (m, 1H),4.95 (m, 1H), 4.59 (m, 2H), 4.41 (m, 2H), 1.40 (m, 3H). 59S δ 8.68 (s,1H), 7.46-7.55 (m, 5H), 4.40 (m, 2H), 4.28-4.35 (m, 2H), 3.88 (m, 1H),3.58 (m, 1H), 3.31 (m, 1H), 1.91-2.02 (m, 1H), 1.52-1.81 (m, 4H), 1.39(m, 3H). 61S δ 8.72 (s, 1H), 7.76 (m, 2H), 7.55 (m, 3H), 4.66 (m, 2H),4.42 (m, 2H), 2.41 (s, 1H), 1.42 (m, 3H). 84S δ 8.62 (s, 1H), 6.81 (m,2H), 6.70 (m, 1H), 5.29 (s, 2H), 4.39 (q, 2H), 3.86 (d, 6H), 2.76 (t,2H), 1.73 (m, 2H), 1.40 (t, 3H), 0.98 (t, 3H). 105S δ 8.64 (s, 1H), 7.42(m, 1H), 7.20 (m, 1H), 7.18 (m, 1H), 7.00 (s, 1H), 5.34 (s, 2H), 4.39(m, 2H), 2.65 (m, 2H), 1.75 (m, 2H), 1.40 (m, 3H), 0.95 (t, 3H). 118S δ8.66 (s, 1H), 7.38 (m, 2H), 7.29 (m, 2H), 4.40 (m, 2H), 4.11 (m, 2H),3.30 (t, 2H), 3.15 (s, 3H), 2.43 (s, 3H), 1.93 (m, 2H), 1.40 (t, 3H).135S δ 8.68 (s, 1H), 7.47 (d, 1H), 6.98 (d, 1H), 4.53 (m, 2H), 4.39 (q,2H), 4.02 (s, 3H), 1.82 (m, 2H), 1.39 (t, 3H), 0.96 (t, 3H). 153S (300MHz) δ 8.51 (s, 1H), 4.23-4.18 (m, 2H), 3.88 (s, 3H), 1.99- 1.95 (m,1H), 1.85-1.77 (m, 2H), 1.36-1.32 (m, 2H), 1.21-1.17 (m, 2H), 1.03 (t,3H). 163S (500 MHz) δ 8.62 (s, 1H), 7.06-6.98 (m, 3H), 4.40 (q, 2H),3.95 (d, 2H), 1.80-1.70 (m, 1H), 1.66-1.55 (m, 3H), 1.46 (d, 2H), 1.40(t, 3H), 1.17-0.96 (m, 3H), 0.70 (dd, 2H). 164S δ 8.59 (s, 1H), 7.55 (m,3H), 7.42 (m, 2H), 4.40 (q, 2H), 3.92 (m, 1H), 3.10 (d, 2H), 2.64 (d,2H), 2.41 (m, 2H), 1.98 (m, 2H), 1.40 (t, 3H). 186S δ 8.57 (s, 1H), 7.71(m, 1H), 7.52 (m, 1H), 7.24 (m, 1H), 4.39 (m, 3H), 4.04 (d, 2H), 3.17(m, 4H), 1.58 (m, 3H), 1.39 (t, 3H). 212S δ 8.80 (s, 1H), 7.14-7.25 (m,1H), 6.95-7.18 (m, 5H), 6.82-6.92 (m, 2H), 3.94 (s, 3H), 3.78 (s, 3H),2.26 (s, 3H). 216S δ 8.57 (s, 1H), 7.64 (m, 2H), 7.43 (m, 2H), 4.40 (q,2H), 3.89 (m, 1H), 3.24 (s, 1H), 2.75 (dd, 2H), 1.78 (d, 2H), 1.63 (m,3H), 1.55 (d, 1H), 1.39 (t, 3H), 0.99 (m, 2H). 242S δ 8.71 (s, 1H), 7.99(m, 2H), 7.93 (d, 2H), 7.62 (m, 2H), 7.53 (dd, 1H), 4.42 (q, 2H), 4.01(m, 2H), 1.71 (m, 2H), 1.42 (t, 3H), 0.75 (t, 3H). 247S δ 8.60 (s, 1H),7.51 (m, 3H), 7.42 (m, 2H), 4.39 (q, 2H), 4.12 (m, 1H), 2.32 (m, 2H),1.98 (m, 2H), 1.39 (t, 3H), 1.18 (m, 12H), 1.02 (m, 3H), 0.66 (m, 3H).257S δ 8.47 (s, 1H), 4.34 (m, 4H), 3.02 (m, 2H), 1.82 (m, 6H), 1.36 (m,3H). ^(a)Mass spectra are reported as the molecular weight of thehighest isotopic abundance parent ion (M + 1) formed by addition of H⁺(molecular weight of 1) to the molecule, observed by mass spectrometryusing atmospheric pressure chemical ionization (AP⁺) unless otherwisenoted. ^(b1)H NMR data are reported in CDCl₃ at 400 MHz unless otherwisenoted; s means singlet, br s means broad singlet, d means doublet, ddmeans doublet of doublet, ddd means doublet of double of doublets, ddtmeans doublet of doublet of triplets, t means triplet, td means tripletof doublets, q means quartet, quin means quintet and sxt means sextet.

Biological Examples of the Invention Test A

Seeds of barnyardgrass (Echinochloa crus-galli), large crabgrass(Digitaria sanguinalis), giant foxtail (Setaria faberii), morning glory(Ipomoea spp.), pigweed (Amaranthus retroflexus), velvetleaf (Abutilontheophrasti), wheat (Triticum aestivum) and corn (Zea mays) were plantedinto a blend of loam soil and sand and treated preemergence with adirected soil spray using test chemicals formulated in a non-phytotoxicsolvent mixture which included a surfactant. At the same time thesespecies were also treated with postemergence applications of testcompounds formulated in the same manner.

Plants ranged in height from two to ten cm and were in the one- totwo-leaf stage for the postemergence treatment. Treated plants anduntreated controls were maintained in a greenhouse for approximately tendays, after which time all treated plants were compared to untreatedcontrols and visually evaluated for injury. Plant response ratings,summarized in Table A, are based on a 0 to 100 scale where 0 is noeffect and 100 is complete control. A dash (-) response means no testresult.

TABLE A Compound 1000 g ai/ha 217 Postemergence Barnyardgrass 90 Corn 40Crabgrass, Large 100 Foxtail, Giant 80 Morningglory 100 Pigweed 100Velvetleaf 100 Wheat 40 Compounds 500 g ai/ha 1 2 3 4 7 8 9 10 11 12 1314 15 16 Postemergence Barnyardgrass 60 100 90 100 70 100 100 90 100 9090 80 40 60 Corn 0 90 10 50 40 50 70 90 20 80 50 20 10 20 Crabgrass,Large 80 100 90 90 70 90 90 100 90 100 90 90 70 40 Foxtail, Giant 40 10060 90 60 100 90 100 90 90 80 90 70 70 Morningglory 90 100 90 100 100 10090 100 90 100 50 100 50 20 Pigweed 80 100 100 100 100 100 100 100 100100 100 100 90 70 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100100 100 100 Wheat 20 20 10 60 40 50 40 60 0 0 60 0 20 10 Compounds 500 gai/ha 17 18 19 20 21 22 23 24 25 26 27 28 29 30 PostemergenceBarnyardgrass 70 90 70 10 10 70 60 70 90 80 90 90 90 30 Corn 10 20 10 100 40 0 30 20 20 30 0 10 0 Crabgrass, Large 70 80 20 10 10 80 60 90 90 90100 80 90 60 Foxtail, Giant 30 90 50 0 0 80 50 90 90 90 90 80 90 40Morningglory 70 100 60 10 0 100 100 100 90 80 70 10 90 50 Pigweed 100100 100 50 50 100 100 100 100 100 100 100 100 80 Velvetleaf 100 100 10070 70 100 100 100 100 100 100 100 100 — Wheat 10 50 0 0 0 0 0 30 0 0 0 00 0 Compounds 500 g ai/ha 31 32 33 34 35 36 37 38 39 40 41 42 43 44Postemergence Barnyardgrass 80 80 100 100 60 100 90 90 90 90 90 90 90100 Corn 20 10 20 30 10 60 40 60 40 50 10 30 50 40 Crabgrass, Large 9090 100 100 80 100 100 100 90 100 70 80 90 90 Foxtail, Giant 90 90 100100 80 100 90 90 90 100 80 70 80 90 Morningglory 70 100 90 100 80 100100 100 90 100 70 80 80 90 Pigweed 100 100 100 100 100 100 100 100 100100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100 100 100 100100 100 100 100 Wheat 0 30 20 30 0 0 0 40 0 0 0 0 0 20 Compounds 500 gai/ha 45 46 47 48 49 50 51 52 53 54 55 56 57 58 PostemergenceBarnyardgrass 100 90 100 90 90 100 90 90 100 60 70 90 90 90 Corn 20 2070 30 20 30 80 70 80 10 10 50 40 20 Crabgrass, Large 90 90 100 100 90 90100 100 100 70 90 90 90 90 Foxtail, Giant 90 90 100 100 80 90 90 100 9060 60 90 90 90 Morningglory 100 70 100 100 100 80 100 100 100 100 90 10060 100 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat40 0 0 20 0 0 0 40 50 0 0 0 10 0 Compounds 500 g ai/ha 59 60 61 62 63 6465 66 67 68 69 70 71 72 Postemergence Barnyardgrass 90 90 90 90 90 90 5090 90 90 100 80 60 90 Corn 30 10 10 70 50 60 0 60 10 10 40 20 20 10Crabgrass, Large 100 100 90 90 90 90 60 90 90 100 100 90 80 90 Foxtail,Giant 90 90 80 90 80 80 40 80 60 70 90 90 60 60 Morningglory 100 90 100100 100 100 60 90 100 90 100 100 100 90 Pigweed 100 100 100 100 100 10060 100 100 100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100100 100 100 100 100 100 100 Wheat 10 50 0 20 0 30 0 0 30 0 10 0 0 0Compounds 500 g ai/ha 73 74 75 76 77 78 79 80 81 82 83 84 85 86Postemergence Barnyardgrass 90 90 90 80 90 70 90 80 100 70 90 10 90 90Corn 60 20 50 20 20 20 60 50 70 20 30 20 80 50 Crabgrass, Large 90 90 9090 80 70 90 90 90 90 90 10 90 90 Foxtail, Giant 90 80 90 70 70 50 80 9090 80 90 0 90 90 Morningglory 100 100 100 90 100 100 100 100 100 100 10090 100 90 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100100 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100Wheat 50 20 50 10 0 0 50 0 30 0 0 0 40 50 Compounds 500 g ai/ha 87 88 8990 91 92 93 94 95 96 97 98 99 100 Postemergence Barnyardgrass 90 90 9090 100 90 90 90 90 90 90 90 90 90 Corn 50 60 10 20 10 20 30 10 10 20 8060 20 0 Crabgrass, Large 90 90 100 90 100 90 100 90 90 100 100 100 10090 Foxtail, Giant 90 90 90 80 80 90 90 80 90 90 80 90 90 90 Morningglory100 100 100 100 100 100 100 100 100 100 100 100 100 100 Pigweed 100 100100 100 100 100 100 100 100 100 100 100 100 100 Velvetleaf 100 100 100100 100 100 100 100 100 100 100 100 100 100 Wheat 60 0 20 40 50 0 0 0 020 20 20 0 30 Compounds 500 g ai/ha 101 102 103 104 105 106 107 108 109110 111 112 113 114 Postemergence Barnyardgrass 90 90 60 40 50 50 90 9090 90 90 90 90 90 Corn 10 20 20 0 10 10 50 40 30 10 30 20 60 50Crabgrass, Large 90 100 40 0 70 70 90 90 100 90 90 90 100 90 Foxtail,Giant 80 90 20 0 20 60 90 90 90 50 90 80 100 80 Morningglory 70 100 100100 80 100 100 100 100 100 100 100 100 100 Pigweed 100 100 100 100 100100 100 100 100 100 100 100 100 100 Velvetleaf 100 100 100 80 100 100100 100 100 100 100 100 100 100 Wheat 0 10 0 0 0 0 10 0 0 0 0 10 60 0Compounds 500 g ai/ha 115 116 117 118 119 120 121 122 123 124 125 126127 128 Postemergence Barnyardgrass 90 100 90 90 90 90 100 80 90 90 9090 90 100 Corn 20 10 50 30 70 50 40 30 70 20 20 60 20 60 Crabgrass,Large 90 80 100 90 90 100 100 90 90 90 90 90 90 90 Foxtail, Giant 80 9080 90 90 90 90 80 80 70 90 80 80 90 Morningglory 100 100 100 100 100 100100 100 100 100 80 100 100 100 Pigweed 100 100 100 100 100 100 100 100100 100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100 100 100100 100 100 100 100 Wheat 0 0 30 10 60 70 60 50 20 0 10 20 0 20Compounds 500 g ai/ha 129 130 131 132 133 134 135 136 138 139 140 141142 143 Postemergence Barnyardgrass 100 100 90 90 90 60 30 80 90 80 9090 90 90 Corn 50 50 30 40 40 20 0 0 20 40 20 30 20 20 Crabgrass, Large90 100 90 70 100 80 70 90 90 80 90 90 90 90 Foxtail, Giant 90 90 90 7090 70 0 50 90 80 90 90 80 80 Morningglory 100 100 100 90 70 60 90 100100 100 100 100 100 100 Pigweed 100 100 100 90 100 80 90 100 100 100 100100 100 90 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100100 100 Wheat 20 30 0 30 40 0 0 0 20 40 0 0 20 10 Compounds 500 g ai/ha144 145 146 147 148 149 150 151 152 153 154 155 156 157 PostemergenceBarnyardgrass 100 100 100 90 100 90 80 90 100 90 90 100 90 100 Corn 3040 30 30 60 30 0 10 50 20 10 40 20 30 Crabgrass, Large 90 90 90 90 90 7050 70 100 90 100 90 80 100 Foxtail, Giant 90 80 90 80 90 80 70 70 100 8090 90 90 100 Morningglory 70 90 90 100 100 100 100 100 100 60 70 100 10030 Pigweed 90 100 100 100 100 100 60 100 100 100 100 100 100 100Velvetleaf 100 100 100 100 100 100 90 100 100 100 100 100 100 100 Wheat0 0 50 60 0 50 20 20 70 10 0 30 20 0 Compounds 500 g ai/ha 158 159 160161 162 163 164 165 166 167 168 169 170 171 Postemergence Barnyardgrass90 100 100 90 100 100 100 80 100 100 100 100 90 90 Corn 50 70 60 10 5020 50 30 40 30 30 30 30 40 Crabgrass, Large 100 90 90 90 100 90 100 5090 90 90 100 90 90 Foxtail, Giant 90 100 80 90 100 50 100 30 90 90 90100 80 90 Morningglory 100 100 100 100 100 100 100 100 — 100 100 100 100100 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat50 60 50 0 50 0 20 0 0 0 50 20 20 50 Compounds 500 g ai/ha 172 173 174175 176 177 178 179 180 181 182 183 184 185 Postemergence Barnyardgrass90 100 100 100 90 100 90 90 100 100 90 90 100 90 Corn 30 20 20 20 10 070 80 40 50 20 80 80 50 Crabgrass, Large 80 90 90 80 60 70 80 100 100 9090 100 100 70 Foxtail, Giant 90 90 60 80 70 40 80 90 100 100 80 100 10080 Morningglory 100 100 60 80 50 10 100 100 100 100 100 70 100 100Pigweed 100 100 100 100 100 100 80 100 100 100 100 100 100 100Velvetleaf 100 100 100 100 90 100 100 100 100 100 100 100 100 100 Wheat20 60 0 0 0 0 30 80 30 60 50 80 50 0 Compounds 500 g ai/ha 186 187 188189 190 191 192 193 194 195 196 197 198 199 Postemergence Barnyardgrass90 100 90 90 100 100 90 100 100 90 90 100 100 100 Corn 60 50 10 40 0 5040 40 10 20 40 50 30 50 Crabgrass, Large 90 100 90 90 90 100 80 100 9090 90 100 100 100 Foxtail, Giant 90 90 80 90 90 100 70 100 50 70 100 10090 100 Morningglory 100 100 100 100 100 100 70 100 100 — 100 100 100 100Pigweed 100 100 100 100 100 90 80 100 100 100 100 100 100 100 Velvetleaf100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 0 0 0 0 050 0 70 0 0 30 0 0 10 Compounds 500 g ai/ha 200 202 203 204 205 206 207208 209 210 211 212 213 214 Postemergence Barnyardgrass 10 100 100 100100 100 90 90 100 90 100 100 100 90 Corn 0 30 30 10 20 0 30 20 40 0 20 020 30 Crabgrass, Large 10 100 70 100 90 100 90 80 100 30 80 30 50 90Foxtail, Giant 10 100 80 100 90 90 90 80 100 70 80 40 40 90 Morningglory60 100 100 100 100 100 80 100 100 100 100 100 100 100 Pigweed 80 100 100100 100 100 100 90 100 100 90 100 100 100 Velvetleaf 100 100 100 100 100100 100 100 100 70 70 70 60 100 Wheat 0 50 30 40 10 0 0 10 0 10 0 0 0 20Compounds 500 g ai/ha 215 216 218 219 220 221 222 223 224 225 226 227228 229 Postemergence Barnyardgrass 100 90 90 90 90 20 80 50 90 100 9090 90 100 Corn 30 0 70 30 30 20 0 20 50 50 60 60 90 40 Crabgrass, Large70 80 70 100 90 20 30 60 100 100 100 100 100 100 Foxtail, Giant 80 70 7090 60 10 40 70 100 90 90 90 90 100 Morningglory 100 90 100 100 100 20 4080 100 100 100 100 100 100 Pigweed 100 90 100 100 100 70 70 70 100 100100 100 100 100 Velvetleaf 100 100 100 100 100 80 90 80 100 100 100 100100 100 Wheat 0 30 0 30 20 0 0 0 60 40 50 0 20 20 Compounds 500 g ai/ha230 231 232 233 234 235 236 237 238 239 240 241 242 243 PostemergenceBarnyardgrass 90 90 90 90 100 100 90 100 100 90 100 90 90 100 Corn 20 4060 80 50 90 50 80 80 30 80 50 20 90 Crabgrass, Large 90 70 60 90 90 10090 100 100 90 100 70 60 90 Foxtail, Giant 50 80 90 90 90 100 90 100 10080 100 90 80 100 Morningglory 90 100 100 100 100 100 100 100 100 100 100100 100 100 Pigweed 90 90 90 100 90 100 100 100 100 90 100 80 30 100Velvetleaf 100 100 80 100 100 100 100 100 100 100 100 100 90 100 Wheat 00 50 60 20 80 40 70 80 0 40 60 30 90 Compounds 500 g ai/ha 244 245 246247 248 249 250 251 252 253 254 255 256 Postemergence Barnyardgrass 100100 100 80 100 100 100 100 90 100 90 100 90 Corn 80 90 90 30 30 20 70 2010 40 10 70 10 Crabgrass, Large 90 90 100 70 80 100 100 90 60 100 70 10080 Foxtail, Giant 90 100 100 30 100 90 100 90 60 100 50 90 70Morningglory 100 100 100 100 100 100 100 100 100 100 50 100 80 Pigweed100 100 100 90 90 100 100 80 90 100 90 100 100 Velvetleaf 100 100 100100 100 100 100 100 90 100 90 100 100 Wheat 70 80 50 0 0 50 20 10 10 200 50 0 Compounds 125 g ai/ha 1 2 3 4 7 8 9 10 11 12 13 14 15 16Postemergence Barnyardgrass 20 100 50 90 30 90 80 90 40 90 30 30 10 20Corn 0 30 0 10 0 10 10 30 0 40 0 0 0 0 Crabgrass, Large 50 90 90 70 5080 70 90 50 90 30 30 20 10 Foxtail, Giant 10 90 30 80 40 90 80 90 70 9030 30 10 30 Morningglory 70 90 80 100 100 90 80 100 90 100 0 20 10 10Pigweed 70 100 100 100 80 100 100 100 90 100 80 80 60 50 Velvetleaf 100100 100 100 100 100 100 100 100 100 100 100 100 70 Wheat 10 0 0 0 0 10 040 0 0 10 0 0 0 Compounds 125 g ai/ha 17 18 19 20 21 22 23 24 25 26 2728 29 30 Postemergence Barnyardgrass 10 20 0 0 0 10 10 10 30 30 50 30 2010 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 10 30 0 0 0 40 3070 40 70 70 40 70 30 Foxtail, Giant 0 40 20 0 0 30 10 70 50 50 80 30 7010 Morningglory 20 40 0 0 0 30 50 70 50 50 60 0 60 30 Pigweed 80 100 8010 0 80 80 90 80 90 100 100 80 70 Velvetleaf 100 100 100 20 30 100 100100 100 100 100 100 100 100 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds125 g ai/ha 31 32 33 34 35 36 37 38 39 40 41 42 43 44 PostemergenceBarnyardgrass 10 20 80 90 10 90 50 60 60 90 50 60 70 90 Corn 0 0 0 0 0 00 0 0 0 0 0 0 0 Crabgrass, Large 50 50 70 90 50 80 70 60 80 90 20 60 7080 Foxtail, Giant 70 30 60 90 40 80 70 50 80 90 20 40 60 80 Morningglory20 50 80 80 — 50 80 100 80 50 10 80 20 80 Pigweed 70 100 90 100 80 90100 100 100 100 100 100 100 100 Velvetleaf 100 100 100 100 100 100 100100 100 100 100 100 100 100 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds125 g ai/ha 45 46 47 48 49 50 51 52 53 54 55 56 57 58 PostemergenceBarnyardgrass 90 80 90 80 60 90 90 90 90 10 50 90 70 50 Corn 0 0 0 0 0 00 0 0 0 0 10 0 0 Crabgrass, Large 60 70 90 90 90 90 90 90 90 40 70 80 8080 Foxtail, Giant 50 60 90 90 50 90 90 90 90 10 20 80 80 70 Morningglory80 60 80 90 100 80 100 100 100 40 90 90 50 80 Pigweed 90 80 90 100 100100 100 90 100 100 90 90 90 100 Velvetleaf 100 100 100 100 100 100 100100 100 100 100 100 100 100 Wheat 0 0 0 0 0 0 0 0 30 0 0 0 0 0 Compounds125 g ai/ha 59 60 61 62 63 64 65 66 67 68 69 70 71 72 PostemergenceBarnyardgrass 90 60 70 80 70 50 10 80 70 80 90 50 0 80 Corn 10 0 0 30 100 0 — — 0 20 0 0 0 Crabgrass, Large 90 90 80 70 80 80 30 70 60 80 80 5030 80 Foxtail, Giant 80 80 50 70 60 60 10 70 30 50 80 50 20 40Morningglory 100 60 100 100 100 90 50 90 100 90 100 100 80 90 Pigweed100 100 100 90 90 90 20 100 100 100 100 100 70 80 Velvetleaf 100 100 100100 100 100 90 100 100 100 100 100 100 100 Wheat 0 20 0 0 0 0 0 0 20 0 00 0 0 Compounds 125 g ai/ha 73 74 75 76 77 78 79 80 81 82 83 84 85 86Postemergence Barnyardgrass 70 80 80 50 80 50 80 30 100 10 70 0 90 90Corn 30 0 0 0 0 0 10 0 10 0 0 0 10 0 Crabgrass, Large 90 90 90 70 60 3080 70 90 40 80 0 90 90 Foxtail, Giant 80 40 80 40 50 20 50 70 80 10 70 070 80 Morningglory 100 90 90 90 90 70 100 100 90 90 100 90 100 90Pigweed 100 100 100 90 100 100 100 100 100 90 90 100 100 100 Velvetleaf100 90 100 100 100 100 100 100 100 100 100 70 100 100 Wheat 10 0 0 0 0 00 0 0 0 0 0 0 0 Compounds 125 g ai/ha 87 88 89 90 91 92 93 94 95 96 9798 99 100 Postemergence Barnyardgrass 80 80 90 80 90 80 90 90 80 90 9080 90 80 Corn 10 0 0 0 0 0 10 0 0 0 50 0 0 0 Crabgrass, Large 90 90 9080 90 90 90 80 90 90 80 90 90 80 Foxtail, Giant 70 60 60 70 80 80 80 3070 70 60 70 80 80 Morningglory 90 90 100 100 100 100 100 100 100 100 100100 100 90 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 10090 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100Wheat 30 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 101 102 103 104105 106 107 108 109 110 111 112 113 114 Postemergence Barnyardgrass 8080 30 10 20 10 90 90 80 60 90 60 70 70 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 10Crabgrass, Large 90 90 10 0 20 40 80 90 90 80 90 80 100 80 Foxtail,Giant 60 80 0 0 0 20 70 60 70 10 60 70 90 60 Morningglory 60 100 100 7010 100 100 100 90 90 100 90 100 90 Pigweed 90 100 100 100 90 80 100 100100 90 100 90 100 100 Velvetleaf 100 100 100 70 100 100 100 100 100 90100 100 100 100 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha115 116 117 118 119 120 121 122 123 124 125 126 127 128 PostemergenceBarnyardgrass 70 80 80 90 80 90 80 60 80 40 70 80 80 100 Corn 0 0 20 0 010 0 0 20 0 0 10 20 20 Crabgrass, Large 60 60 80 90 80 90 80 70 80 70 7090 80 90 Foxtail, Giant 50 60 70 80 70 80 90 70 70 50 70 70 70 90Morningglory 90 100 100 100 90 100 100 90 100 100 80 100 90 100 Pigweed100 100 100 100 100 90 100 100 100 90 90 90 90 100 Velvetleaf 100 70 100100 100 100 100 100 100 100 100 100 100 100 Wheat 0 0 0 0 50 20 30 0 0 00 0 0 0 Compounds 125 g ai/ha 129 130 131 132 133 134 135 136 138 139140 141 142 143 Postemergence Barnyardgrass 90 100 90 10 20 10 10 30 9060 90 90 70 70 Corn 20 10 0 0 10 0 0 0 20 20 0 20 0 10 Crabgrass, Large90 70 90 20 40 50 40 80 70 70 90 80 70 70 Foxtail, Giant 90 80 80 0 2040 0 30 60 50 80 80 30 60 Morningglory 100 100 100 90 40 0 70 100 50 100100 70 100 90 Pigweed 100 100 100 60 80 70 80 80 100 90 90 90 90 70Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat0 0 0 0 20 0 0 0 0 20 0 0 0 0 Compounds 125 g ai/ha 144 145 146 147 148149 150 151 152 153 154 155 156 157 Postemergence Barnyardgrass 70 70100 80 90 70 40 60 100 80 90 90 90 90 Corn 0 30 20 20 0 0 0 0 0 0 0 2020 0 Crabgrass, Large 50 70 80 80 70 40 20 30 90 90 70 70 70 80 Foxtail,Giant 40 60 70 70 60 60 40 20 80 70 60 80 80 90 Morningglory 30 90 90100 100 100 100 40 100 50 30 100 100 10 Pigweed 80 100 100 100 90 70 30100 100 100 60 100 100 90 Velvetleaf 100 100 100 100 100 100 50 100 100100 100 100 100 100 Wheat 0 0 20 20 0 20 0 0 20 0 0 0 0 0 Compounds 125g ai/ha 158 159 160 161 162 163 164 165 166 167 168 169 170 171Postemergence Barnyardgrass 90 90 90 30 100 50 100 0 80 60 30 90 40 50Corn 10 0 20 0 0 0 10 0 30 30 20 0 20 30 Crabgrass, Large 70 90 90 60 8060 90 20 40 60 50 90 60 60 Foxtail, Giant 70 90 70 40 70 20 100 20 60 9050 80 50 60 Morningglory 70 100 100 60 100 10 100 50 100 60 100 100 100100 Pigweed 100 100 100 80 100 80 100 80 70 90 100 100 80 100 Velvetleaf100 100 100 100 100 100 100 100 100 100 100 100 100 100 Wheat 0 10 0 030 0 0 0 0 0 0 20 0 20 Compounds 125 g ai/ha 172 173 174 175 176 177 178179 180 181 182 183 184 185 Postemergence Barnyardgrass 90 90 90 50 5080 80 60 90 100 70 60 90 70 Corn 20 0 10 0 0 0 0 10 10 10 0 10 10 0Crabgrass, Large 60 70 70 40 10 30 50 60 90 90 80 80 80 50 Foxtail,Giant 60 70 20 30 10 0 50 40 70 100 50 80 90 50 Morningglory 90 100 3010 0 0 50 60 40 30 100 40 50 100 Pigweed 100 100 100 100 100 100 60 90100 100 80 100 100 90 Velvetleaf 100 100 100 100 80 90 90 100 100 100100 100 100 90 Wheat 0 0 0 0 0 0 0 40 0 30 0 50 0 0 Compounds 125 gai/ha 186 187 188 189 190 191 192 193 194 195 196 197 198 199Postemergence Barnyardgrass 80 90 70 90 90 90 60 90 90 70 80 80 70 90Corn 0 0 0 10 0 0 0 10 0 0 10 20 0 0 Crabgrass, Large 90 90 80 90 90 7030 100 60 40 50 70 70 70 Foxtail, Giant 80 80 40 80 80 80 50 90 30 30 7080 60 100 Morningglory 100 100 90 100 100 90 — 100 90 60 100 100 100 100Pigweed 100 100 90 100 100 80 60 100 100 90 80 100 90 100 Velvetleaf 100100 100 100 100 100 70 100 100 100 100 100 100 100 Wheat 0 0 0 0 0 0 040 0 0 0 0 0 0 Compounds 125 g ai/ha 200 202 203 204 205 206 207 208 209210 211 212 213 214 Postemergence Barnyardgrass 0 90 80 100 90 90 60 3080 40 50 50 20 80 Corn 0 10 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 1070 30 60 60 60 60 30 50 10 40 10 20 80 Foxtail, Giant 0 80 30 30 40 5060 30 60 10 50 0 10 50 Morningglory 50 100 100 30 100 100 40 50 30 50 7050 60 80 Pigweed 60 100 100 100 90 90 100 80 60 90 70 100 80 90Velvetleaf 100 100 90 100 100 100 100 100 100 70 60 70 70 100 Wheat 0 200 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 215 216 218 219 220 221222 223 224 225 226 227 228 229 Postemergence Barnyardgrass 90 10 80 9090 10 10 0 90 90 90 90 90 90 Corn 0 0 0 0 0 0 0 0 10 10 10 10 50 0Crabgrass, Large 40 40 20 80 50 10 0 0 70 90 90 90 90 80 Foxtail, Giant40 30 40 50 20 0 0 0 70 70 90 90 90 90 Morningglory 100 70 80 100 100 1030 60 100 100 100 100 100 100 Pigweed 90 90 100 100 100 40 40 50 100 100100 100 100 100 Velvetleaf 100 90 100 100 100 80 60 50 100 100 100 100100 100 Wheat 0 20 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 230 231232 233 234 235 236 237 238 239 240 241 242 243 PostemergenceBarnyardgrass 70 70 60 90 80 90 90 100 100 90 100 90 50 100 Corn 0 0 1060 20 80 20 40 40 30 40 20 0 70 Crabgrass, Large 80 50 20 90 40 100 8080 90 80 90 50 20 90 Foxtail, Giant 30 60 60 90 70 90 70 90 90 70 90 8050 100 Morningglory 70 90 100 100 100 100 100 100 100 100 100 100 40 100Pigweed 80 80 70 100 70 100 80 90 100 80 90 70 20 100 Velvetleaf 100 9070 100 100 100 100 100 100 100 100 100 50 100 Wheat 0 0 20 20 0 50 0 2050 0 20 40 0 70 Compounds 125 g ai/ha 244 245 246 247 248 249 250 251252 253 254 255 256 Postemergence Barnyardgrass 90 90 70 30 90 90 50 8080 100 0 90 40 Corn 40 40 0 0 0 0 0 0 0 10 0 30 0 Crabgrass, Large 90 9070 40 50 90 60 50 30 80 20 90 30 Foxtail, Giant 90 100 80 0 50 80 90 5040 60 10 90 20 Morningglory 100 100 90 100 100 100 100 100 80 100 20 10030 Pigweed 100 100 90 70 80 90 100 70 70 90 60 90 90 Velvetleaf 100 100100 100 100 100 100 100 70 100 50 100 100 Wheat 40 40 0 0 0 10 0 0 0 0 010 0 Compound 1000 g ai/ha 217 Preemergence Barnyardgrass 80 Corn 0Crabgrass, Large 100 Foxtail, Giant 80 Morningglory 70 Pigweed 100Velvetleaf 100 Wheat 30 Compounds 500 g ai/ha 1 2 3 4 7 8 9 10 11 12 1314 15 16 Preemergence Barnyardgrass 10 70 60 70 10 80 100 90 70 70 90 7090 70 Corn 0 0 0 20 0 20 0 0 0 0 20 0 0 20 Crabgrass, Large 70 100 80 9040 100 100 100 90 90 100 90 90 70 Foxtail, Giant 10 90 10 70 20 90 90100 50 90 90 90 70 70 Morningglory 50 90 100 70 40 70 90 90 70 90 0 6060 0 Pigweed 100 100 100 90 80 90 100 100 100 100 100 100 90 50Velvetleaf 80 100 90 100 100 90 100 100 100 90 100 100 90 40 Wheat 0 0 020 0 20 0 50 0 0 40 0 20 0 Compounds 500 g ai/ha 17 18 19 20 21 22 23 2425 26 27 28 29 30 Preemergence Barnyardgrass 80 100 90 20 0 100 70 90 8060 80 70 100 40 Corn 0 20 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 100100 80 30 20 90 90 100 100 90 90 60 100 60 Foxtail, Giant 20 90 30 20 1080 20 100 90 70 90 30 100 10 Morningglory 10 70 50 0 0 70 70 80 60 70 8080 80 60 Pigweed 90 100 90 — 70 90 70 100 80 100 90 100 100 80Velvetleaf 100 100 100 50 0 100 100 100 100 100 100 80 100 70 Wheat 0 400 0 0 0 0 20 20 0 0 0 0 0 Compounds 500 g ai/ha 31 32 33 34 35 36 37 3839 40 41 42 43 44 Preemergence Barnyardgrass 40 90 90 100 0 50 30 90 90100 80 60 80 100 Corn 0 0 30 0 0 0 0 30 0 0 0 0 0 0 Crabgrass, Large 9090 100 100 60 80 50 100 90 100 80 90 100 90 Foxtail, Giant 40 90 90 10010 60 50 80 90 90 30 40 70 90 Morningglory 50 80 50 60 20 30 30 70 60 8020 50 10 70 Pigweed 80 100 90 100 100 80 100 100 90 90 90 100 100 90Velvetleaf 70 70 80 100 70 100 90 100 90 100 80 100 100 100 Wheat 0 2010 0 0 20 0 20 0 0 0 0 0 0 Compounds 500 g ai/ha 45 46 47 48 49 50 51 5253 54 55 56 57 58 Preemergence Barnyardgrass 80 50 90 100 60 90 90 100100 10 10 90 90 90 Corn 0 0 0 0 0 0 0 10 0 0 0 0 0 0 Crabgrass, Large100 80 100 100 90 100 100 100 100 30 50 90 100 90 Foxtail, Giant 80 6090 90 50 80 100 100 100 0 0 90 90 80 Morningglory 90 70 90 80 80 80 9090 90 0 60 90 80 100 Pigweed 100 90 100 100 90 100 100 100 100 90 100100 100 100 Velvetleaf 100 70 100 100 90 90 90 100 90 70 60 100 100 100Wheat 20 20 0 0 0 0 0 0 10 0 0 0 0 0 Compounds 500 g ai/ha 59 60 61 6263 64 65 66 67 68 69 70 71 72 Preemergence Barnyardgrass 90 90 90 90 9090 10 70 40 50 60 10 0 60 Corn 0 10 0 20 0 0 0 0 0 0 0 0 0 20 Crabgrass,Large 100 100 100 90 100 90 80 100 90 100 100 90 50 100 Foxtail, Giant80 90 60 70 80 70 40 80 50 60 70 60 10 30 Morningglory 90 80 80 100 70 00 30 50 50 50 10 0 70 Pigweed 100 100 90 100 100 100 0 100 90 100 100100 90 90 Velvetleaf 100 100 100 90 90 90 50 100 80 100 100 80 70 100Wheat 0 40 0 10 0 0 0 0 0 0 10 0 0 0 Compounds 500 g ai/ha 73 74 75 7677 78 79 80 81 82 83 84 85 86 Preemergence Barnyardgrass 70 60 80 30 5030 70 10 90 10 90 0 100 100 Corn 0 0 0 0 0 0 0 0 0 0 20 0 10 —Crabgrass, Large 100 90 100 100 90 50 100 90 100 100 100 0 100 —Foxtail, Giant 70 40 70 30 20 10 50 60 80 40 90 0 90 100 Morningglory 8060 90 50 70 0 50 30 70 60 60 10 80 60 Pigweed 100 100 100 100 90 100 10090 100 100 100 100 — — Velvetleaf 100 90 100 70 100 50 100 100 100 90100 40 — 100 Wheat 30 0 0 20 0 0 30 0 20 0 30 0 40 — Compounds 500 gai/ha 87 88 89 90 91 92 93 94 95 96 97 98 99 100 PreemergenceBarnyardgrass 90 90 80 70 100 100 100 30 80 100 100 60 90 90 Corn 0 0 00 0 0 0 0 0 10 0 0 0 0 Crabgrass, Large 100 — 90 100 100 100 100 90 90100 100 100 100 90 Foxtail, Giant 80 100 70 60 70 80 80 40 60 80 90 8080 80 Morningglory 80 70 70 70 80 80 90 40 90 80 80 80 80 80 Pigweed — —100 100 90 100 100 100 100 100 100 100 100 100 Velvetleaf 100 100 100100 100 100 100 70 100 100 100 100 100 80 Wheat 40 10 30 0 20 0 0 0 0 00 0 0 0 Compounds 500 g ai/ha 101 102 103 104 105 106 107 108 109 110111 112 113 114 Preemergence Barnyardgrass 70 90 20 0 0 50 90 90 70 6090 80 90 90 Corn 0 0 0 0 0 0 — 0 0 0 0 0 — 0 Crabgrass, Large 90 100 800 50 80 100 90 90 80 100 100 100 100 Foxtail, Giant 50 100 60 0 50 70 9040 30 10 70 60 90 80 Morningglory 80 80 60 0 — 80 100 90 70 70 80 80 8080 Pigweed 80 100 100 90 90 90 100 100 100 90 100 100 100 100 Velvetleaf100 100 90 40 70 60 100 90 100 70 100 70 100 100 Wheat 0 0 0 0 0 0 0 0 00 0 0 0 20 Compounds 500 g ai/ha 115 116 117 118 119 120 121 122 123 124125 126 127 128 Preemergence Barnyardgrass 80 70 90 90 100 100 100 100100 60 90 100 100 100 Corn 0 0 20 0 30 30 30 0 30 0 0 20 0 0 Crabgrass,Large 80 70 100 90 100 100 100 100 100 90 100 100 100 100 Foxtail, Giant70 60 70 50 100 100 100 100 100 40 80 90 90 90 Morningglory 80 40 90 7090 90 70 80 — 80 0 90 80 — Pigweed 100 100 100 100 100 100 100 100 100100 90 100 100 100 Velvetleaf 90 60 90 80 100 100 100 100 100 100 100100 100 100 Wheat 0 0 20 0 60 70 50 40 20 0 0 20 0 30 Compounds 500 gai/ha 129 130 131 132 133 134 135 136 138 139 140 141 142 143Preemergence Barnyardgrass 100 90 100 100 100 10 0 60 90 90 100 100 8090 Corn 0 30 0 20 20 0 0 0 20 20 0 0 0 0 Crabgrass, Large 90 100 100 100100 30 40 60 70 100 90 100 80 90 Foxtail, Giant 80 90 80 90 80 30 0 0 7070 90 80 20 70 Morningglory 90 80 80 30 0 30 50 60 0 80 50 30 50 70Pigweed 100 100 100 80 100 60 80 100 90 100 100 100 100 90 Velvetleaf 9090 100 80 100 70 70 100 80 90 100 100 60 100 Wheat 0 0 0 10 20 0 0 0 2010 0 0 0 0 Compounds 500 g ai/ha 144 145 146 147 148 149 150 151 152 153154 155 156 157 Preemergence Barnyardgrass 20 90 100 100 30 50 0 100 10080 40 90 80 50 Corn 0 20 30 0 0 20 0 0 30 20 0 30 20 0 Crabgrass, Large30 100 100 100 50 80 10 50 100 100 50 90 50 70 Foxtail, Giant 10 70 9090 10 60 0 60 90 70 30 60 50 50 Morningglory 10 80 — 90 0 40 0 30 80 700 0 0 0 Pigweed 90 100 100 100 60 100 0 70 100 100 80 90 80 50Velvetleaf 70 100 100 100 80 70 0 70 100 100 80 100 50 100 Wheat 0 20 4020 0 20 0 20 50 20 0 0 0 0 Compounds 500 g ai/ha 158 159 160 161 162 163164 165 166 167 168 169 170 171 Preemergence Barnyardgrass 80 90 80 90100 20 80 0 20 30 20 50 60 70 Corn 20 40 20 0 0 0 0 0 0 0 0 20 0 20Crabgrass, Large 100 100 100 90 100 10 90 0 70 90 80 40 70 100 Foxtail,Giant 80 90 70 80 90 10 70 0 20 50 70 50 70 80 Morningglory 80 50 — 4080 0 50 0 0 0 70 20 70 60 Pigweed 100 100 100 100 100 60 100 0 40 90 5050 50 80 Velvetleaf 80 100 30 90 100 50 70 0 100 100 60 50 80 100 Wheat10 20 20 0 50 0 0 0 0 0 0 0 20 40 Compounds 500 g ai/ha 172 173 174 175176 177 178 179 180 181 182 183 184 185 Preemergence Barnyardgrass 80 6040 30 30 10 50 70 80 100 90 100 90 50 Corn 0 10 20 0 0 20 0 0 0 0 20 020 0 Crabgrass, Large 90 100 60 50 20 10 70 100 100 100 100 100 100 30Foxtail, Giant 60 40 40 50 50 20 50 90 70 80 80 90 90 50 Morningglory 50— 0 10 20 — 40 40 — 30 80 50 60 30 Pigweed 100 90 90 100 100 50 40 90100 100 100 100 90 70 Velvetleaf 80 100 70 50 50 40 60 100 100 100 100100 100 50 Wheat 0 20 0 0 0 0 0 60 20 20 50 50 0 0 Compounds 500 g ai/ha186 187 188 189 190 191 192 193 194 195 196 197 198 199 PreemergenceBarnyardgrass 60 90 30 90 100 80 30 90 40 10 50 40 50 90 Corn 0 0 0 0 030 40 0 0 0 20 30 20 30 Crabgrass, Large 80 90 70 80 90 100 40 100 40 5070 60 90 100 Foxtail, Giant 60 90 40 60 90 90 40 90 — 30 80 50 70 90Morningglory 90 90 80 80 70 70 0 90 20 0 40 60 30 80 Pigweed 100 70 80100 100 100 50 100 100 10 30 100 100 100 Velvetleaf 100 100 80 100 100100 60 100 70 50 50 90 80 100 Wheat 0 0 0 0 0 20 20 50 0 20 20 20 20 20Compounds 500 g ai/ha 200 202 203 204 205 206 207 208 209 210 211 212213 214 Preemergence Barnyardgrass 0 100 70 80 10 20 50 80 50 70 70 9030 60 Corn 0 40 20 20 0 0 0 20 20 0 0 0 0 0 Crabgrass, Large 0 100 70100 90 60 100 100 70 50 90 40 50 90 Foxtail, Giant 0 100 90 90 80 60 8070 60 90 50 50 30 70 Morningglory — 100 70 80 60 0 70 70 30 50 10 80 6080 Pigweed 20 100 100 100 90 80 100 100 70 100 60 90 90 90 Velvetleaf 60100 80 90 80 60 100 90 100 60 60 70 60 100 Wheat 0 40 30 40 0 0 0 20 0 00 0 0 30 Compounds 500 g ai/ha 215 216 218 219 220 221 222 223 224 225226 227 228 229 Preemergence Barnyardgrass 20 20 100 100 90 0 60 70 9090 100 100 100 70 Corn 0 20 0 0 10 0 0 0 20 20 0 10 50 0 Crabgrass,Large 60 80 80 100 90 10 20 80 100 100 100 100 100 100 Foxtail, Giant 3060 50 80 40 10 60 90 70 80 90 80 90 60 Morningglory 70 30 80 80 70 0 40— 30 80 80 80 80 80 Pigweed 90 50 90 100 100 60 0 90 100 100 100 100 100100 Velvetleaf 70 30 90 90 100 30 60 60 80 100 100 100 100 100 Wheat 0 00 20 0 0 0 0 30 30 10 10 0 0 Compounds 500 g ai/ha 230 231 232 233 234235 236 237 238 239 240 241 242 243 Preemergence Barnyardgrass 80 60 50100 80 100 90 90 100 80 — 90 0 100 Corn 0 20 0 0 20 70 10 50 50 0 40 200 60 Crabgrass, Large 90 90 40 100 90 100 100 100 100 100 100 90 10 100Foxtail, Giant 50 60 70 80 60 90 70 90 90 70 80 70 0 100 Morningglory 2080 40 90 10 90 80 80 90 50 0 30 0 90 Pigweed 80 80 90 100 60 90 90 100100 100 100 50 0 100 Velvetleaf 80 60 60 80 90 100 100 100 100 100 80 600 100 Wheat 0 0 30 40 20 40 30 30 40 30 40 40 0 70 Compounds 500 g ai/ha244 245 246 247 248 249 250 251 252 253 254 255 256 PreemergenceBarnyardgrass 100 100 100 0 30 40 40 20 0 20 10 100 70 Corn 40 20 50 020 0 0 0 0 — 0 0 0 Crabgrass, Large 100 100 100 0 70 80 90 80 20 80 5090 80 Foxtail, Giant 100 90 90 0 20 40 60 40 10 70 30 50 30 Morningglory80 60 60 0 40 70 60 40 10 70 — 60 50 Pigweed 100 90 100 0 40 100 100 6040 80 0 90 90 Velvetleaf 100 100 100 0 60 90 90 70 50 90 20 100 80 Wheat40 20 50 0 20 0 10 0 0 20 0 0 0 Compounds 125 g ai/ha 1 2 3 4 7 8 9 1011 12 13 14 15 16 Preemergence Barnyardgrass 0 10 30 10 0 10 0 30 0 1010 10 10 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 10 80 50 200 40 90 90 20 50 60 30 40 40 Foxtail, Giant 0 50 0 10 0 40 40 70 10 2050 40 40 30 Morningglory — 60 0 0 0 0 20 10 0 30 0 10 0 0 Pigweed 20 10080 90 10 90 50 100 60 80 40 100 30 30 Velvetleaf 60 60 80 40 60 50 70 9060 70 80 90 40 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha17 18 19 20 21 22 23 24 25 26 27 28 29 30 Preemergence Barnyardgrass 010 10 0 0 10 0 10 20 0 10 10 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0Crabgrass, Large 20 60 20 0 0 40 10 30 60 20 30 20 20 0 Foxtail, Giant 040 10 0 0 20 0 40 50 30 30 0 30 0 Morningglory 0 20 0 0 0 20 0 20 0 1020 20 40 0 Pigweed 80 70 80 0 — 70 50 90 50 60 70 80 50 0 Velvetleaf 4030 50 0 0 30 40 90 80 20 60 20 20 20 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0Compounds 125 g ai/ha 31 32 33 34 35 36 37 38 39 40 41 42 43 44Preemergence Barnyardgrass 0 0 10 10 0 10 0 10 10 10 0 0 10 30 Corn 0 00 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 0 20 80 90 10 10 10 30 60 60 2040 50 80 Foxtail, Giant 0 10 30 60 0 10 10 10 50 50 10 10 10 30Morningglory 0 0 0 10 — 0 0 0 40 10 0 0 0 20 Pigweed 40 30 80 90 10 0 5050 60 70 90 90 90 60 Velvetleaf 10 20 50 50 0 60 50 70 70 70 30 70 60 70Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 45 46 47 48 4950 51 52 53 54 55 56 57 58 Preemergence Barnyardgrass 40 0 10 20 20 5010 40 40 0 0 50 40 30 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large50 30 70 90 60 90 30 90 90 0 0 80 90 70 Foxtail, Giant 0 0 50 70 20 5030 80 70 0 0 70 70 50 Morningglory 20 10 60 40 30 40 — 30 80 0 30 50 20— Pigweed 80 60 80 90 80 90 90 100 90 80 50 90 90 70 Velvetleaf 60 40 7080 80 80 70 100 80 60 60 80 80 70 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0Compounds 125 g ai/ha 59 60 61 62 63 64 65 66 67 68 69 70 71 72Preemergence Barnyardgrass 40 60 30 10 10 10 0 20 0 0 10 0 0 10 Corn 0 00 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 90 90 60 60 90 80 10 90 30 7090 40 10 70 Foxtail, Giant 50 60 10 60 50 50 0 — — — 40 30 0 0Morningglory — — 60 90 10 0 0 0 30 20 0 0 0 — Pigweed 90 90 80 80 100 800 90 90 90 100 60 — 50 Velvetleaf 100 80 60 70 80 60 30 70 70 70 70 7050 90 Wheat 0 0 0 0 — 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 73 74 7576 77 78 79 80 81 82 83 84 85 86 Preemergence Barnyardgrass 0 30 40 0 200 0 0 50 0 30 0 50 20 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 — Crabgrass, Large70 70 90 50 50 10 50 50 90 — 70 0 100 — Foxtail, Giant 50 0 50 0 0 0 010 30 10 40 0 — — Morningglory 10 40 60 0 — 0 0 0 0 0 20 0 50 0 Pigweed100 90 100 50 80 50 100 60 100 90 80 90 — — Velvetleaf 80 70 90 20 70 2070 50 100 50 70 0 70 — Wheat 10 0 0 0 0 0 0 0 0 0 0 0 0 — Compounds 125g ai/ha 87 88 89 90 91 92 93 94 95 96 97 98 99 100 PreemergenceBarnyardgrass 20 10 20 40 60 60 80 0 40 90 60 0 10 40 Corn 0 0 0 0 0 0 00 0 0 0 0 0 0 Crabgrass, Large — — 60 60 90 90 90 30 50 100 100 90 60 80Foxtail, Giant — — 20 30 40 70 60 0 30 50 60 40 40 50 Morningglory 50 500 0 20 0 80 10 70 80 70 70 — 70 Pigweed — — 90 80 90 100 100 70 90 100100 100 90 80 Velvetleaf 100 80 70 70 100 90 90 40 90 100 100 90 80 60Wheat 10 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 101 102 103 104105 106 107 108 109 110 111 112 113 114 Preemergence Barnyardgrass 20 400 0 0 10 40 30 10 20 30 0 10 30 Corn 0 0 0 0 0 0 20 0 0 0 0 0 0 0Crabgrass, Large 70 80 40 0 30 70 90 70 40 40 90 60 70 90 Foxtail, Giant30 80 0 0 30 40 60 30 0 0 — 20 70 40 Morningglory 80 80 20 0 0 50 70 8040 40 50 0 30 0 Pigweed 70 60 90 80 80 80 100 90 90 80 100 20 100 100Velvetleaf 80 80 60 0 0 40 100 80 70 60 90 40 100 70 Wheat 0 0 0 0 0 0 00 0 0 0 0 0 0 Compounds 125 g ai/ha 115 116 117 118 119 120 121 122 123124 125 126 127 128 Preemergence Barnyardgrass 0 10 50 30 70 70 20 30 5020 10 70 40 10 Corn 0 0 0 0 20 20 0 0 0 0 0 0 0 0 Crabgrass, Large 20 3060 60 100 100 90 90 100 60 80 90 90 80 Foxtail, Giant 20 10 20 10 90 9080 30 50 10 40 60 50 60 Morningglory 60 0 40 10 60 30 0 40 70 60 0 70 1080 Pigweed 70 60 90 90 100 100 80 100 90 100 90 100 100 80 Velvetleaf 6030 70 70 90 80 80 100 70 70 60 80 70 80 Wheat 0 0 0 0 20 0 0 0 0 0 0 0 00 Compounds 125 g ai/ha 129 130 131 132 133 134 135 136 138 139 140 141142 143 Preemergence Barnyardgrass 30 20 50 10 10 0 0 0 20 40 60 60 1040 Corn 0 20 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 70 40 80 50 50 0 020 40 90 70 80 30 50 Foxtail, Giant 40 20 60 20 40 0 0 0 30 20 40 40 010 Morningglory — 10 — 0 0 — 20 30 0 0 30 0 0 10 Pigweed 100 90 100 1040 0 40 80 50 70 80 70 90 70 Velvetleaf 80 80 80 50 50 70 40 70 20 60 8070 20 70 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 144 145146 147 148 149 150 151 152 153 154 155 156 157 PreemergenceBarnyardgrass 0 20 60 70 10 20 0 20 50 40 0 10 0 0 Corn 0 0 0 0 0 0 0 00 20 0 0 0 0 Crabgrass, Large 10 50 60 100 0 30 0 10 90 80 10 60 10 20Foxtail, Giant 0 30 30 70 0 10 0 20 60 20 10 30 10 10 Morningglory 0 010 40 0 0 0 — 60 20 0 0 0 0 Pigweed 0 70 70 90 0 80 0 50 100 100 30 9070 0 Velvetleaf 20 90 70 80 30 40 0 50 60 100 40 60 0 60 Wheat 0 0 0 0 00 0 0 20 0 0 0 0 0 Compounds 125 g ai/ha 158 159 160 161 162 163 164 165166 167 168 169 170 171 Preemergence Barnyardgrass 20 30 40 10 10 0 10 00 0 0 0 0 20 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 70 80 8050 90 0 30 0 10 20 30 40 10 70 Foxtail, Giant 10 60 20 50 30 0 40 0 0 1010 40 10 30 Morningglory 0 0 70 0 0 0 10 — 0 0 0 0 0 0 Pigweed 100 10080 90 100 0 60 0 0 10 10 0 30 50 Velvetleaf 50 70 60 70 60 10 40 0 40 700 20 10 80 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 20 Compounds 125 g ai/ha 172173 174 175 176 177 178 179 180 181 182 183 184 185 PreemergenceBarnyardgrass 10 0 0 0 10 0 0 0 30 20 70 20 20 0 Corn 0 0 10 0 0 0 0 0 00 0 0 0 0 Crabgrass, Large 10 40 20 30 0 0 10 20 80 90 100 90 30 0Foxtail, Giant 10 20 0 0 10 0 10 10 30 30 50 60 30 0 Morningglory 0 0 00 0 0 0 0 0 0 70 20 10 — Pigweed 10 50 30 60 60 0 0 50 90 100 90 90 70 0Velvetleaf 50 70 20 40 10 10 0 50 80 70 70 100 80 0 Wheat 0 0 0 0 0 0 00 0 0 0 0 0 0 Compounds 125 g ai/ha 186 187 188 189 190 191 192 193 194195 196 197 198 199 Preemergence Barnyardgrass 0 20 0 20 10 10 10 80 0 00 0 0 20 Corn 0 0 0 0 0 0 40 0 0 0 0 0 0 20 Crabgrass, Large 30 30 30 3060 50 10 90 20 0 0 0 10 60 Foxtail, Giant 20 30 10 30 60 40 0 90 — 0 0 070 60 Morningglory 20 80 70 — — 0 0 80 — 0 0 0 0 70 Pigweed 50 60 60 7070 80 0 100 50 0 0 20 10 80 Velvetleaf 60 70 70 70 70 60 0 100 30 0 0 400 90 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 200 202 203204 205 206 207 208 209 210 211 212 213 214 Preemergence Barnyardgrass 020 30 30 0 0 10 10 0 10 10 10 0 10 Corn 0 20 0 20 0 0 0 0 0 0 0 0 0 0Crabgrass, Large 0 50 20 40 20 10 60 80 20 10 10 0 0 30 Foxtail, Giant 050 30 20 10 0 30 40 10 20 20 10 10 30 Morningglory 0 0 0 0 0 0 0 0 0 0 00 — 0 Pigweed 0 90 100 100 10 30 80 60 0 60 40 60 50 70 Velvetleaf 0 7050 50 10 0 70 60 60 40 30 50 40 90 Wheat 0 0 0 20 0 0 0 0 0 0 0 0 0 0Compounds 125 g ai/ha 215 216 218 219 220 221 222 223 224 225 226 227228 229 Preemergence Barnyardgrass 0 0 20 40 10 0 0 0 0 20 30 50 40 0Corn 0 0 0 0 0 0 0 0 20 0 0 0 0 0 Crabgrass, Large 0 0 10 50 20 0 20 3070 60 90 90 100 80 Foxtail, Giant 10 0 0 10 0 0 30 30 20 40 70 40 50 50Morningglory 0 0 0 20 0 0 0 10 — 30 60 50 70 40 Pigweed 20 0 20 90 80 00 60 70 90 100 80 100 90 Velvetleaf 0 0 50 30 40 20 0 0 50 80 80 90 100100 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 230 231 232233 234 235 236 237 238 239 240 241 242 243 Preemergence Barnyardgrass10 0 0 30 0 90 50 20 70 20 40 10 0 70 Corn 0 0 0 0 0 20 0 0 0 0 0 0 0 30Crabgrass, Large 30 40 10 40 60 100 80 40 90 70 50 20 0 100 Foxtail,Giant 40 0 0 20 10 70 40 40 50 20 40 10 0 90 Morningglory 0 10 0 50 — 8070 10 40 — 0 0 0 70 Pigweed — 50 0 70 50 90 80 30 100 70 20 20 0 100Velvetleaf 60 50 0 60 30 100 80 80 90 80 60 20 0 90 Wheat 0 0 0 0 0 10 00 0 0 0 0 0 30 Compounds 125 g ai/ha 244 245 246 247 248 249 250 251 252253 254 255 256 Preemergence Barnyardgrass 30 40 10 0 0 0 0 0 0 10 0 100 Corn 20 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 90 80 100 0 10 40 3020 10 30 0 20 10 Foxtail, Giant 70 80 90 0 10 20 30 10 0 20 0 0 0Morningglory 30 20 20 0 0 30 10 0 0 40 0 40 0 Pigweed 100 80 100 0 0 8060 0 0 20 0 70 0 Velvetleaf 50 70 90 0 20 60 50 50 20 50 0 60 20 Wheat 00 0 0 0 0 0 0 0 0 0 0 0

Test B

Seeds of plant species selected from blackgrass (Alopecurusmyosuroides), downy bromegrass (Bromus tectorum), green foxtail (Setariaviridis), Italian ryegrass (Lolium multiflorum), wheat (Triticumaestivum), wild oat (Avena fatua), deadnettle (henbit deadnettle, Lamiumamplexicaule), galium (catchweed bedstraw, Galium aparine), bermudagrass(Cynodon dactylon), Surinam grass (Brachiaria decumbens), cocklebur(Xanthium strumarium), corn (Zea mays), large crabgrass (Digitariasanguinalis), woolly cupgrass (Eriochloa villosa), giant foxtail(Setaria faberii), goosegrass (Eleusine indica), johnsongrass (Sorghumhalepense), kochia (Kochia scoparia), lambsquarters (Chenopodium album),morning glory (Ipomoea coccinea), nightshade (eastern black nightshade,Solanum ptycanthum), yellow nutsedge (Cyperus esculentus), pigweed(Amaranthus retroflexus), ragweed (common ragweed, Ambrosia elatior),Russian thistle (Salsola kali), soybean (Glycine max), sunflower (commonoilseed sunflower, Helianthus annuus) and velvetleaf (Abutilontheophrasti) were planted into a blend of loam soil and sand and treatedpreemergence with test compounds formulated in a non-phytotoxic solventmixture which included a surfactant.

At the same time, plants selected from these crop and weed species andalso winter barley (Hordeum vulgare), canarygrass (Phalaris minor),chickweed (Stellaria media) and windgrass (Apera spica-venti) wereplanted in pots containing Redi-Earth® planting medium (Scotts Company,14111 Scottslawn Road, Marysville, Ohio 43041) comprising spaghnum peatmoss, vermiculite, wetting agent and starter nutrients and treated withpostemergence applications of some of the test chemicals formulated inthe same manner. Plants ranged in height from 2 to 18 cm (1- to 4-leafstage) for postemergence treatments.

Plant species in the flooded paddy test consisted of rice (Oryzasativa), umbrella sedge (Cyperus difformis), ducksalad (Heterantheralimosa) and barnyardgrass (Echinochloa crus-galli) grown to the 2-leafstage for testing. At the time of treatment, test pots were flooded withwater to 3 cm above the soil surface, treated by application of testcompounds directly to the paddy water, and then maintained at that waterdepth for the duration of the test.

Treated plants and controls were maintained in a greenhouse for 13 to 15days, after which time all treated plants were visually evaluated andcompared to controls. Plant response ratings, summarized in Table B, arebased on a scale of 0 to 100 where 0 is no effect and 100 is completecontrol. A dash (-) response means no test result.

TABLE B Compounds 250 g ai/ha 1 2 3 4 7 8 9 10 11 12 13 14 15 16 FloodBarnyardgrass 0 0 0 20 0 45 50 0 25 0 35 0 35 10 Ducksalad 0 78 70 85 090 75 80 80 55 95 40 60 75 Rice 0 8 0 0 0 50 0 0 25 0 25 0 0 10 Sedge,Umbrella 0 75 60 90 0 95 75 55 85 65 85 40 30 50 Compounds 250 g ai/ha17 18 19 20 21 22 23 24 25 26 27 28 29 30 Flood Barnyardgrass 25 50 15 00 0 0 20 0 0 40 20 30 0 Ducksalad 45 90 90 75 75 60 45 75 0 85 85 85 8550 Rice 15 25 0 15 0 0 15 0 0 0 0 0 0 0 Sedge, Umbrella 80 85 95 60 6565 45 75 0 85 85 80 80 50 Compounds 250 g ai/ha 31 32 33 34 35 36 37 3839 40 41 42 43 44 Flood Barnyardgrass 0 40 40 0 0 15 0 0 30 40 30 0 2030 Ducksalad 75 95 95 65 0 40 60 65 90 90 75 50 80 90 Rice 0 30 50 0 —35 20 0 15 25 0 20 40 40 Sedge, Umbrella 75 90 85 40 0 20 40 40 90 85 8030 80 90 Compounds 250 g ai/ha 45 46 47 48 49 50 51 52 53 54 55 56 57 58Flood Barnyardgrass 30 0 20 35 0 60 55 55 75 0 20 35 25 0 Ducksalad 9020 95 85 70 85 95 70 75 40 50 50 60 0 Rice 20 10 25 65 15 20 60 60 85 025 20 25 0 Sedge, Umbrella 85 65 85 75 85 95 90 40 90 40 60 75 75 0Compounds 250 g ai/ha 59 60 61 62 63 64 65 66 67 68 69 70 71 72 FloodBarnyardgrass 45 40 20 0 10 0 0 45 0 20 30 20 0 30 Ducksalad 40 60 0 3040 60 0 20 0 40 20 0 0 0 Rice 15 15 0 0 10 0 0 20 0 30 0 20 0 20 Sedge,Umbrella 75 85 0 0 0 40 0 50 0 0 40 20 25 30 Compounds 250 g ai/ha 73 7475 76 77 78 79 80 81 82 83 84 85 86 Flood Barnyardgrass 0 40 60 0 65 030 30 60 20 40 0 65 60 Ducksalad 0 0 50 0 40 20 40 30 40 20 50 20 65 65Rice 0 0 45 0 15 20 20 15 15 20 30 0 20 40 Sedge, Umbrella 0 60 50 0 4040 30 40 40 50 50 50 80 85 Compounds 250 g ai/ha 87 88 89 90 91 92 93 9495 96 97 98 99 100 Flood Barnyardgrass 60 60 40 30 65 45 85 60 70 85 7550 55 75 Ducksalad 20 80 100 90 100 85 80 30 20 75 70 0 80 85 Rice 70 5015 0 15 40 45 35 30 15 40 40 60 — Sedge, Umbrella 70 65 85 80 100 85 9085 75 90 80 75 85 85 Compounds 250 g ai/ha 101 102 103 104 105 106 107108 109 110 111 112 113 114 Flood Barnyardgrass 40 70 0 0 0 15 60 30 2040 60 40 15 40 Ducksalad 30 85 0 0 0 0 40 70 100 75 75 95 70 75 Rice 2035 0 0 0 20 45 10 25 30 30 15 0 20 Sedge, Umbrella 65 75 0 0 0 0 85 9580 75 85 90 70 40 Compounds 250 g ai/ha 115 116 117 118 119 120 121 122123 124 125 126 127 128 Flood Barnyardgrass 65 75 75 70 50 65 70 40 7030 60 75 75 40 Ducksalad 85 85 100 100 70 85 80 0 95 0 70 85 80 100 Rice20 0 15 15 35 40 55 15 40 20 0 15 35 35 Sedge, Umbrella 90 90 95 85 7575 70 45 85 40 90 85 80 75 Compounds 250 g ai/ha 129 130 131 132 133 134135 136 138 139 140 141 142 143 Flood Barnyardgrass 60 85 50 30 0 0 0 2525 35 45 50 10 20 Ducksalad 100 100 85 100 100 0 40 75 80 90 85 85 80 90Rice 30 25 55 0 0 0 0 20 15 30 40 35 0 0 Sedge, Umbrella 60 100 85 100100 0 0 50 80 85 85 85 80 65 Compounds 250 g ai/ha 144 145 146 147 148151 152 153 154 155 156 158 161 162 Flood Barnyardgrass 20 25 30 75 5055 75 45 40 45 60 60 30 55 Ducksalad 100 80 100 100 100 100 100 100 10095 100 100 80 100 Rice 25 0 35 15 50 50 60 65 75 45 35 85 50 90 Sedge,Umbrella 100 80 90 80 95 100 100 95 100 100 100 100 60 100 Compounds 250g ai/ha 164 178 179 183 184 185 186 187 188 189 190 191 192 193 FloodBarnyardgrass 0 80 30 35 25 0 30 80 0 70 30 25 0 50 Ducksalad 85 100 10095 100 75 100 100 85 100 100 100 75 100 Rice 35 70 65 0 15 0 65 70 15 6015 0 20 65 Sedge, Umbrella 90 95 95 90 95 60 90 100 85 100 95 85 60 90Compounds 250 g ai/ha 194 195 196 197 198 199 200 203 204 206 207 208209 210 Flood Barnyardgrass 15 20 30 30 35 25 38 20 60 0 20 25 20 40Ducksalad 80 85 95 85 95 90 85 95 100 90 50 75 85 90 Rice 0 15 65 45 500 23 0 60 20 15 0 20 25 Sedge, Umbrella 65 65 80 85 80 85 70 85 95 85 7070 80 80 Compounds 250 g ai/ha 211 212 213 214 215 216 217 218 219 220221 222 223 224 Flood Barnyardgrass 35 50 30 20 40 0 0 40 60 40 20 0 030 Ducksalad 85 95 100 95 85 95 40 95 90 100 70 65 0 75 Rice 15 10 20 1515 0 20 15 75 70 15 0 0 60 Sedge, Umbrella 80 95 90 85 90 100 40 85 8585 75 40 0 75 Compounds 250 g ai/ha 226 227 228 229 230 231 232 233 234235 236 237 238 239 Flood Barnyardgrass 95 60 80 30 40 40 50 65 0 75 2030 40 15 Ducksalad 40 80 80 40 0 0 85 100 70 100 70 100 100 80 Rice 6555 60 20 45 0 0 50 0 55 0 45 0 0 Sedge, Umbrella 60 85 85 70 75 75 80 8540 80 40 100 80 75 Compounds 250 g ai/ha 243 244 245 246 248 249 250 251252 253 254 255 256 Flood Barnyardgrass 85 75 65 60 40 0 10 20 0 20 15 00 Ducksalad 100 100 100 100 90 90 75 80 0 90 100 80 85 Rice 75 85 90 650 15 0 10 0 20 0 0 0 Sedge, Umbrella 100 100 100 100 85 90 70 75 0 85 8060 75 Compounds 125 g ai/ha 1 2 3 4 7 8 9 10 11 12 13 14 16 17 FloodBarnyardgrass 0 0 0 0 0 20 0 0 0 0 0 0 0 25 Ducksalad 0 58 70 75 0 85 6075 65 35 0 30 75 30 Rice 0 0 0 0 0 15 0 0 20 0 0 0 0 0 Sedge, Umbrella 045 60 80 0 85 70 55 40 50 60 0 40 70 Compounds 125 g ai/ha 18 19 20 2122 23 33 34 35 36 37 38 49 50 Flood Barnyardgrass 20 0 0 0 0 0 30 0 0 00 0 0 35 Ducksalad 65 85 65 70 30 45 80 30 0 0 50 60 40 85 Rice 25 0 0 00 0 20 0 0 20 0 0 10 15 Sedge, Umbrella 50 85 50 60 40 40 50 0 0 0 30 300 85 Compounds 125 g ai/ha 51 52 53 54 55 56 57 58 59 60 61 62 63 64Flood Barnyardgrass 40 40 55 0 20 20 20 0 20 30 0 0 0 0 Ducksalad 85 4075 30 0 40 40 0 0 40 0 0 40 50 Rice 25 50 60 0 15 15 15 0 15 0 0 0 0 0Sedge, Umbrella 85 30 90 0 40 60 50 0 50 75 0 0 0 0 Compounds 125 gai/ha 65 66 67 68 69 70 71 72 76 79 80 81 82 83 Flood Barnyardgrass 0 00 0 20 0 0 0 0 20 25 40 15 15 Ducksalad 0 0 0 30 0 0 0 0 0 15 30 15 0 40Rice 0 0 0 20 0 0 0 20 0 15 0 15 15 0 Sedge, Umbrella 0 30 0 0 0 20 0 00 0 30 30 40 40 Compounds 125 g ai/ha 84 85 86 87 88 89 90 91 92 93 9495 96 97 Flood Barnyardgrass 0 55 50 55 40 30 15 60 20 75 40 65 80 60Ducksalad 0 60 55 20 75 100 80 90 70 80 25 0 50 30 Rice 0 15 20 60 40 00 15 25 20 20 30 15 0 Sedge, Umbrella 30 80 70 50 40 85 75 100 70 80 8550 85 70 Compounds 125 g ai/ha 98 99 100 101 102 103 104 105 106 108 109110 111 123 Flood Barnyardgrass 30 20 60 40 60 0 0 0 0 15 20 20 50 55Ducksalad 0 75 85 30 80 0 0 0 0 60 65 75 75 90 Rice 0 0 35 0 20 0 0 0 200 20 30 0 30 Sedge, Umbrella 75 65 80 30 65 0 0 0 0 60 75 50 80 75Compounds 125 g ai/ha 124 125 126 127 128 129 130 132 133 142 143 144145 146 Flood Barnyardgrass 0 40 60 65 15 10 0 0 0 0 0 0 0 0 Ducksalad 060 85 60 95 90 80 80 100 80 80 75 80 80 Rice 20 0 0 25 10 0 0 0 0 0 0 200 0 Sedge, Umbrella 20 90 80 60 60 60 75 60 95 65 0 95 60 80 Compounds125 g ai/ha 147 148 151 152 153 154 155 156 157 158 161 162 163 164Flood Barnyardgrass 45 15 30 50 35 0 20 40 0 20 0 40 0 0 Ducksalad 80 90100 100 100 70 85 80 70 100 0 100 60 0 Rice 10 20 15 30 55 60 25 20 0 4045 90 20 20 Sedge, Umbrella 40 85 100 85 80 95 85 100 75 100 0 100 70 0Compounds 125 g ai/ha 166 167 168 170 171 172 173 174 175 176 177 178179 180 Flood Barnyardgrass 20 20 0 30 20 20 15 0 20 0 15 60 20 15Ducksalad 60 70 30 45 70 60 75 95 95 75 70 100 95 75 Rice 0 0 0 20 0 015 0 0 20 20 70 25 30 Sedge, Umbrella 70 60 20 35 80 75 85 95 85 85 7595 85 65 Compounds 125 g ai/ha 181 182 183 184 185 186 190 191 192 193194 195 196 197 Flood Barnyardgrass 70 0 0 20 0 30 20 0 0 45 10 0 20 20Ducksalad 90 85 80 100 75 90 40 75 75 85 50 70 95 80 Rice 65 0 0 15 0 4515 0 0 30 0 0 40 30 Sedge, Umbrella 85 75 65 80 65 80 30 80 50 70 0 5075 75 Compounds 125 g ai/ha 198 199 200 203 204 207 208 209 210 211 212213 215 216 Flood Barnyardgrass 30 15 23 0 25 0 15 0 20 25 0 0 30 0Ducksalad 85 85 85 95 90 0 40 85 90 85 90 90 85 90 Rice 20 0 10 0 0 15 010 20 0 0 0 0 0 Sedge, Umbrella 80 75 43 75 90 60 40 70 75 70 90 85 7580 Compounds 125 g ai/ha 218 219 220 221 223 224 226 227 228 229 230 235236 237 Flood Barnyardgrass 30 20 30 0 0 0 95 50 75 0 20 50 0 0Ducksalad 85 65 85 70 0 0 30 75 75 0 0 100 60 90 Rice 10 70 50 0 0 0 6045 35 0 30 45 0 0 Sedge, Umbrella 85 60 20 75 0 0 50 85 75 50 40 80 0 55Compounds 125 g ai/ha 238 239 243 244 245 246 248 249 250 251 253 254255 256 Flood Barnyardgrass 30 0 75 40 40 20 0 0 10 0 0 10 0 0 Ducksalad80 70 100 100 100 100 80 80 70 50 85 85 60 80 Rice 0 0 95 60 50 65 0 0 00 0 0 0 0 Sedge, Umbrella 65 40 100 100 100 100 75 85 65 65 75 75 50 75Compounds 62 g ai/ha 1 2 3 4 7 8 9 10 11 12 13 14 15 16 FloodBarnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 20 0 Ducksalad 0 40 0 40 0 85 3020 0 25 0 20 0 40 Rice 0 0 0 0 0 0 0 0 10 0 0 0 0 0 Sedge, Umbrella 0 050 65 0 65 30 40 0 40 0 0 0 0 Compounds 62 g ai/ha 17 18 19 20 21 22 2324 25 26 27 28 29 30 Flood Barnyardgrass 20 20 0 0 0 0 0 0 0 0 0 10 0 0Ducksalad 30 50 75 60 70 20 35 20 0 75 75 70 70 20 Rice 0 15 0 0 0 0 0 00 0 0 0 0 0 Sedge, Umbrella 70 30 70 40 50 30 30 0 0 75 75 70 70 20Compounds 62 g ai/ha 31 32 33 34 35 36 37 38 39 40 41 42 43 44 FloodBarnyardgrass 0 10 20 0 0 0 0 0 0 0 0 0 20 0 Ducksalad 60 75 75 0 0 0 3020 80 0 70 30 70 80 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 20 Sedge, Umbrella 6075 30 0 0 0 20 0 90 70 70 30 30 80 Compounds 62 g ai/ha 45 46 47 48 4950 51 52 53 54 55 56 57 58 Flood Barnyardgrass 0 0 0 0 0 0 20 0 40 0 2015 0 0 Ducksalad 20 20 65 0 0 75 30 0 65 0 0 20 0 0 Rice 15 10 15 0 0 1015 0 20 0 10 0 0 0 Sedge, Umbrella 70 45 70 40 0 75 40 30 85 0 30 40 0 0Compounds 62 g ai/ha 59 60 61 62 63 64 65 66 67 68 69 70 71 72 FloodBarnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 0 20 30 0 0 00 0 0 0 0 Rice 15 0 0 0 0 0 0 0 0 15 0 0 0 0 Sedge, Umbrella 40 30 0 0 00 0 0 0 0 0 0 0 0 Compounds 62 g ai/ha 73 74 75 76 77 78 79 80 81 82 8384 85 86 Flood Barnyardgrass 0 0 20 0 30 0 0 20 0 0 0 0 25 40 Ducksalad0 0 30 0 30 0 0 20 0 0 30 0 50 55 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0Sedge, Umbrella 0 30 0 0 40 30 0 20 0 0 30 0 75 30 Compounds 62 g ai/ha87 88 89 90 91 92 93 94 95 96 97 98 99 100 Flood Barnyardgrass 45 20 200 20 0 60 0 35 65 40 30 20 45 Ducksalad 30 40 90 65 90 30 55 20 0 0 30 040 75 Rice 20 0 0 0 15 0 15 0 20 15 0 0 0 30 Sedge, Umbrella 20 30 85 6095 65 75 70 20 75 40 65 50 75 Compounds 62 g ai/ha 101 102 103 104 105106 107 108 109 110 111 112 113 114 Flood Barnyardgrass 40 60 0 0 0 0 400 0 0 40 35 10 20 Ducksalad 30 40 0 0 0 0 0 50 60 40 30 85 25 65 Rice 015 0 0 0 0 20 0 0 0 0 0 0 0 Sedge, Umbrella 20 40 0 0 0 0 60 40 60 35 7585 40 30 Compounds 62 g ai/ha 115 116 117 118 119 120 121 122 123 124125 126 127 128 Flood Barnyardgrass 50 65 65 50 30 20 30 20 40 0 25 4540 10 Ducksalad 85 80 — 100 30 30 45 0 80 0 40 80 30 95 Rice 20 0 0 0 200 0 0 20 15 0 0 15 0 Sedge, Umbrella 70 75 95 70 25 40 30 20 70 0 35 7020 30 Compounds 62 g ai/ha 129 130 131 132 133 134 135 136 138 139 140141 142 143 Flood Barnyardgrass 0 0 20 0 0 0 0 20 0 10 20 20 0 0Ducksalad 90 80 40 50 60 0 30 55 70 75 50 75 0 80 Rice 0 0 25 0 0 0 0 150 10 0 0 0 0 Sedge, Umbrella 0 60 20 0 60 0 0 45 70 70 75 80 0 0Compounds 62 g ai/ha 144 145 146 147 148 151 152 153 154 155 156 158 161162 Flood Barnyardgrass 0 0 0 10 0 15 25 0 0 0 20 20 0 25 Ducksalad 6080 60 60 90 80 90 65 50 60 65 75 0 100 Rice 20 0 0 0 10 0 20 35 0 0 3030 50 25 Sedge, Umbrella 65 0 50 40 80 85 0 0 95 60 95 85 0 100Compounds 62 g ai/ha 164 178 179 183 184 185 186 187 188 189 190 191 192193 Flood Barnyardgrass 0 20 10 0 0 0 20 45 0 30 0 0 0 20 Ducksalad 0 7590 65 100 70 90 95 70 100 20 85 60 50 Rice 0 20 0 0 15 0 20 15 0 20 15 00 15 Sedge, Umbrella 0 85 80 50 80 75 80 95 80 95 0 75 40 30 Compounds62 g ai/ha 194 195 196 197 198 199 200 203 204 206 207 208 209 210 FloodBarnyardgrass 0 0 0 0 0 0 0 0 15 0 0 0 0 0 Ducksalad 50 50 60 65 50 8583 75 70 70 0 30 50 85 Rice 0 0 0 0 20 0 0 0 0 0 0 0 0 0 Sedge, Umbrella0 0 30 70 20 70 33 65 75 60 40 40 50 75 Compounds 62 g ai/ha 211 212 213214 215 216 217 218 219 220 221 222 223 224 Flood Barnyardgrass 0 0 0 00 0 0 0 0 0 0 0 0 0 Ducksalad — 85 85 0 75 90 0 80 20 40 65 50 0 0 Rice0 0 0 0 0 0 0 0 0 15 0 0 0 0 Sedge, Umbrella 0 85 80 0 0 65 40 80 40 060 30 0 0 Compounds 62 g ai/ha 226 227 228 229 230 231 232 233 234 235236 237 238 239 Flood Barnyardgrass 60 40 40 0 0 40 30 20 0 20 0 0 0 0Ducksalad 0 — 50 0 0 0 85 100 20 95 0 65 40 0 Rice 40 30 20 0 20 0 0 250 0 0 0 0 0 Sedge, Umbrella 40 85 75 0 30 0 80 70 0 70 0 45 0 0Compounds 62 g ai/ha 243 244 245 246 248 249 250 251 252 253 254 255 256Flood Barnyardgrass 30 20 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 85 80 100 10080 65 30 0 0 75 85 50 40 Rice 60 0 50 30 0 0 0 0 0 0 0 0 0 Sedge,Umbrella 90 0 100 85 65 60 65 50 0 65 50 20 40 Compounds 31 g ai/ha 1 23 4 7 8 9 10 11 12 13 14 16 17 Flood Barnyardgrass 0 0 0 0 0 0 0 0 0 0 00 0 0 Ducksalad 0 15 0 20 0 30 0 0 0 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 0 00 0 0 0 Sedge, Umbrella 0 0 40 50 0 30 0 0 0 20 0 0 0 0 Compounds 31 gai/ha 18 19 20 21 22 23 33 34 35 36 37 38 49 50 Flood Barnyardgrass 10 00 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 20 0 60 60 0 20 60 0 0 0 0 0 0 70 Rice10 0 0 0 0 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 0 0 0 40 0 20 20 0 0 0 0 00 75 Compounds 31 g ai/ha 51 52 53 54 55 56 57 58 59 60 61 62 63 64Flood Barnyardgrass 15 0 20 0 0 10 0 0 0 0 0 0 0 0 Ducksalad 0 0 40 0 00 0 0 0 0 0 0 0 30 Rice 10 0 15 0 0 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 3020 40 0 0 30 0 0 30 0 0 0 0 0 Compounds 31 g ai/ha 65 66 67 68 69 70 7172 76 79 80 81 82 83 Flood Barnyardgrass 0 0 0 0 0 0 0 0 0 0 15 0 0 0Ducksalad 0 0 0 0 0 0 0 0 0 0 0 0 0 20 Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0Sedge, Umbrella 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 31 g ai/ha 84 8586 87 88 89 90 91 92 93 94 95 96 97 Flood Barnyardgrass 0 25 30 20 0 200 15 0 30 0 20 60 30 Ducksalad 0 40 0 20 30 45 50 65 20 40 0 0 0 30 Rice0 0 0 0 0 0 0 0 0 0 0 0 10 0 Sedge, Umbrella 0 50 20 0 0 30 50 75 65 7020 0 50 30 Compounds 31 g ai/ha 98 99 100 101 102 103 104 105 106 108109 110 111 123 Flood Barnyardgrass 0 0 20 20 15 0 0 0 0 0 0 0 0 30Ducksalad 0 30 35 20 30 0 0 0 0 40 50 0 30 30 Rice 0 0 0 0 10 0 0 0 0 00 0 0 0 Sedge, Umbrella 40 50 40 0 30 0 0 0 0 0 50 30 0 40 Compounds 31g ai/ha 124 125 126 127 128 129 130 132 133 142 143 144 145 146 FloodBarnyardgrass 0 0 20 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 20 75 0 90 0 60 060 0 80 50 80 0 Rice 0 0 0 0 0 0 0 0 0 0 0 15 0 0 Sedge, Umbrella 0 2550 0 0 0 40 0 0 0 0 50 0 0 Compounds 31 g ai/ha 147 148 151 152 153 154155 156 157 158 161 162 163 164 Flood Barnyardgrass 0 0 0 15 0 0 0 0 020 0 20 0 0 Ducksalad 60 90 80 0 0 0 0 0 50 50 0 98 30 0 Rice 0 20 20 2035 0 0 30 0 20 25 0 10 0 Sedge, Umbrella 0 80 85 0 0 0 60 0 40 70 0 9570 0 Compounds 31 g ai/ha 166 167 168 170 171 172 173 174 175 176 177178 179 180 Flood Barnyardgrass 0 0 0 0 0 0 0 0 0 0 0 20 0 0 Ducksalad 00 0 0 40 20 30 80 75 40 30 75 90 60 Rice 0 0 0 15 0 0 0 0 0 15 15 0 0 15Sedge, Umbrella 50 20 0 0 70 0 0 85 75 70 60 55 40 20 Compounds 31 gai/ha 181 182 183 184 185 186 190 191 192 193 194 195 196 197 FloodBarnyardgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 85 60 30 95 75 90 2065 60 40 40 0 40 65 Rice 0 0 0 15 0 10 15 0 0 0 0 0 0 0 Sedge, Umbrella75 50 0 65 65 70 0 60 0 0 0 0 20 65 Compounds 31 g ai/ha 198 199 200 203204 207 208 209 210 211 212 213 215 216 Flood Barnyardgrass 0 0 0 0 10 00 0 0 0 0 0 0 0 Ducksalad 40 85 38 40 50 0 0 0 75 50 85 75 70 50 Rice 150 0 0 0 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 20 60 30 0 70 0 0 0 50 0 80 650 0 Compounds 31 g ai/ha 218 219 220 221 223 224 226 227 228 229 230 235236 237 Flood Barnyardgrass 0 0 0 0 0 0 50 20 15 0 0 0 0 0 Ducksalad 750 30 20 0 0 0 — 40 0 0 95 0 0 Rice 0 0 0 0 0 0 20 20 0 0 0 0 0 0 Sedge,Umbrella 75 20 0 0 0 0 30 80 65 0 0 0 0 0 Compounds 31 g ai/ha 238 239243 244 245 246 248 249 250 251 253 254 255 256 Flood Barnyardgrass 0 00 0 0 0 0 0 0 0 0 0 0 0 Ducksalad 0 0 0 35 100 85 75 0 30 0 60 45 0 30Rice 0 0 45 0 50 0 0 0 0 0 0 0 0 0 Sedge, Umbrella 0 0 0 0 60 0 50 0 0 060 30 0 30 Compounds 250 g ai/ha 1 3 4 7 8 9 10 11 12 14 24 26 27 29Postemergence Barley 0 0 10 0 20 35 5 10 0 40 70 0 20 0 Bermudagrass 6580 100 70 100 98 95 100 100 80 100 75 100 100 Blackgrass 5 5 50 5 20 7050 40 20 5 50 40 50 50 Bromegrass, Downy 10 45 55 5 10 50 20 45 20 70 7540 30 45 Canarygrass 0 5 80 0 85 60 40 90 40 50 60 60 50 40 Chickweed 90100 100 100 100 98 98 100 100 80 100 85 80 85 Cocklebur 85 100 100 70100 45 98 100 100 98 100 100 98 98 Corn 0 15 85 10 80 80 65 85 75 70 8550 70 60 Crabgrass, Large 65 90 100 60 100 95 80 100 90 85 100 80 60 80Cupgrass, Woolly 20 55 100 65 100 85 75 95 80 80 95 85 80 85 Deadnettle— — — — — — — — — — — — — — Foxtail, Giant 50 65 100 60 100 100 95 10098 95 95 95 90 95 Foxtail, Green 40 50 60 40 95 95 70 98 70 85 95 95 9090 Galium — — — — — — — — — — — — — — Goosegrass 80 95 98 35 100 100 9898 100 85 98 95 98 95 Johnsongrass 20 15 98 0 100 95 75 98 75 80 80 7080 45 Kochia 45 95 100 50 100 85 20 98 65 — 100 — 100 — Lambsquarters 90100 100 75 100 95 95 98 98 85 100 98 98 98 Morningglory 65 70 95 20 10075 55 80 95 95 90 75 90 98 Nutsedge, Yellow 45 80 80 0 85 70 75 60 80 5070 35 55 70 Oat, Wild 10 50 50 10 35 55 40 70 20 50 80 60 65 80 Pigweed90 100 100 98 100 100 100 98 100 98 80 98 100 85 Ragweed 75 100 100 85100 100 98 100 100 98 98 100 100 100 Ryegrass, Italian 0 5 20 20 50 4520 40 5 50 50 45 10 45 Soybean 80 90 100 85 100 98 98 100 100 90 100 98100 98 Surinam Grass 20 65 90 25 80 85 80 85 85 55 80 60 80 85Velvetleaf 90 100 100 98 100 98 85 100 100 100 98 98 90 98 Wheat 5 30 7015 35 30 5 45 0 20 50 30 30 40 Windgrass 5 5 75 5 40 80 40 98 50 50 8060 60 50 Compounds 250 g ai/ha 33 34 36 37 38 39 40 42 44 45 46 47 48 49Postemergence Barley 0 30 — 0 35 10 10 5 15 5 0 35 10 0 Bermudagrass 9898 100 100 100 100 100 98 98 100 90 — 100 98 Blackgrass 30 40 15 30 4020 15 20 30 25 10 30 30 30 Bromegrass, Downy 20 50 65 45 85 0 85 25 8550 25 55 70 5 Canarygrass 5 50 50 30 45 20 35 0 40 30 0 40 45 0Chickweed 100 100 100 100 100 100 100 95 100 100 98 100 100 90 Cocklebur95 95 — — — 98 — 95 98 95 90 100 98 85 Corn 15 50 85 75 90 65 90 45 8580 75 — 85 15 Crabgrass, Large 98 98 98 90 100 90 100 90 98 85 75 100 9585 Cupgrass, Woolly 90 95 98 100 100 90 98 55 95 80 45 100 95 55Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 95 95 98 100 10095 100 85 98 98 85 98 98 75 Foxtail, Green 90 95 90 95 95 90 95 85 90 9585 95 95 90 Galium — — — — — — — — — — — — — — Goosegrass 85 95 95 95 9575 98 95 95 90 80 98 98 70 Johnsongrass 40 100 100 85 100 98 100 65 95100 75 — 95 10 Kochia 98 100 65 65 100 95 75 100 95 98 30 100 100 90Lambsquarters 100 100 100 100 100 100 100 100 98 100 95 100 100 98Morningglory 85 95 75 95 100 95 85 98 80 90 80 95 80 85 Nutsedge, Yellow80 65 60 65 55 45 — 70 55 60 75 70 70 70 Oat, Wild 55 70 85 80 85 40 9025 85 70 30 60 85 40 Pigweed 100 98 98 100 100 100 100 100 100 100 80100 100 98 Ragweed 98 98 95 98 95 98 98 85 98 98 80 95 98 90 Ryegrass,Italian 45 40 15 30 65 20 10 15 35 35 10 50 30 0 Soybean 100 100 100 100100 100 100 95 95 98 90 98 98 85 Surinam Grass 90 85 95 95 95 70 100 6595 95 90 100 98 70 Velvetleaf 100 100 100 100 100 95 100 98 100 95 90100 100 98 Wheat 5 55 5 5 60 20 35 10 30 30 0 15 30 30 Windgrass 60 8085 70 90 — 90 — — — 50 — — 30 Compounds 250 g ai/ha 50 51 52 53 55 56 5859 61 62 63 64 66 67 Postemergence Barley 5 50 25 70 0 — 10 10 0 30 0 350 30 Bermudagrass 100 98 100 98 90 100 100 100 90 90 95 98 95 85Blackgrass 15 55 30 50 10 20 40 60 5 50 50 15 15 10 Bromegrass, Downy 2060 70 60 0 60 50 45 5 50 40 85 25 5 Canarygrass 5 98 85 90 0 40 85 70 05 0 60 0 5 Chickweed 98 95 98 100 90 98 90 100 98 80 95 100 98 100Cocklebur 90 90 85 90 75 95 90 100 85 75 95 95 45 90 Corn 25 85 80 85 1070 80 75 15 80 45 90 75 75 Crabgrass, Large 98 90 98 100 85 95 90 100 7585 90 98 70 95 Cupgrass, Woolly 85 90 95 98 20 85 95 95 60 65 65 98 7575 Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 95 85 90 95 7595 98 95 75 80 80 100 95 90 Foxtail, Green 95 100 100 100 80 100 100 7080 85 90 100 98 95 Galium — — — — — — — — — — — — — — Goosegrass 90 8585 85 75 90 90 95 80 75 75 90 95 80 Johnsongrass 70 98 95 100 20 100 100100 10 10 15 100 65 10 Kochia 100 35 65 80 85 100 25 75 85 80 65 80 9885 Lambsquarters 100 98 95 98 98 100 100 100 98 100 98 100 100 100Morningglory 80 100 85 98 85 100 90 80 80 75 75 90 100 100 Nutsedge,Yellow 75 80 65 75 65 75 75 75 65 55 60 25 70 70 Oat, Wild 30 90 95 85 545 85 80 5 40 20 98 10 10 Pigweed 100 100 98 100 95 100 100 100 98 100100 100 100 100 Ragweed 98 95 85 98 98 75 98 95 90 80 80 90 60 90Ryegrass, Italian 0 30 60 45 0 50 70 80 0 50 10 30 10 5 Soybean 95 95 9895 75 98 95 95 50 95 85 98 98 98 Surinam Grass 85 90 98 98 60 100 98 9075 70 75 98 98 25 Velvetleaf 100 95 100 98 100 98 95 98 98 100 98 100100 100 Wheat 15 30 35 50 10 0 0 60 10 30 10 55 0 25 Windgrass 80 85 10095 5 85 70 70 20 50 60 100 80 5 Compounds 250 g ai/ha 68 70 71 72 73 7475 77 79 80 81 82 83 85 Postemergence Barley 30 90 5 0 10 0 0 0 55 75 55 5 20 Bermudagrass 98 98 98 85 90 98 98 95 85 55 95 95 90 90 Blackgrass20 50 5 0 30 45 20 5 45 10 30 15 0 50 Bromegrass, Downy 40 70 30 20 6035 50 5 65 80 50 30 60 30 Canarygrass 35 98 20 0 40 0 0 0 50 70 20 35 2560 Chickweed 100 100 98 90 100 100 100 98 98 100 100 100 100 98Cocklebur 90 40 95 95 80 95 95 85 98 65 90 100 90 98 Corn 80 75 15 10 8560 55 75 75 65 65 15 25 85 Crabgrass, Large 98 100 95 90 95 95 100 85 9595 98 90 98 95 Cupgrass, Woolly 75 90 100 50 65 75 80 40 75 75 90 75 9590 Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 90 98 95 80 9085 95 80 95 95 98 95 98 98 Foxtail, Green 95 98 98 90 95 85 90 80 98 9895 90 98 98 Galium — — — — — — — — — — — — — — Goosegrass 95 95 90 70 8085 98 85 80 85 80 85 95 85 Johnsongrass 100 98 100 45 75 85 75 10 75 45100 95 100 98 Kochia 98 98 65 90 90 98 100 95 80 60 100 75 95 90Lambsquarters 100 100 98 100 100 98 100 98 100 100 100 100 100 100Morningglory 100 100 80 90 95 100 95 90 100 100 100 100 100 100Nutsedge, Yellow 80 60 25 75 70 70 75 80 80 75 80 55 85 85 Oat, Wild 7095 5 40 95 80 60 5 75 50 55 10 10 60 Pigweed 100 100 100 100 100 100 100100 100 100 100 100 100 100 Ragweed 95 80 95 95 85 90 95 85 98 75 100 9598 98 Ryegrass, Italian 50 70 5 30 70 35 60 10 55 5 55 10 5 45 Soybean98 98 98 95 95 95 98 70 98 95 98 98 95 95 Surinam Grass 90 100 85 100 8575 85 80 90 65 100 80 90 85 Velvetleaf 100 100 95 100 100 100 100 100100 100 100 95 100 98 Wheat 10 35 5 10 50 50 25 10 40 35 25 5 0 35Windgrass 85 100 60 65 98 95 90 25 90 80 70 50 30 95 Compounds 250 gai/ha 86 87 88 89 90 91 92 93 94 95 96 97 98 99 Postemergence Barley 655 80 20 20 40 0 5 5 0 5 5 15 30 Bermudagrass 95 100 85 95 85 95 85 85 9890 98 98 98 98 Blackgrass 55 40 10 30 30 50 5 30 20 5 40 50 50 15Bromegrass, Downy 50 80 60 5 10 30 20 0 0 0 10 10 40 25 Canarygrass 8535 90 60 30 75 0 10 35 0 45 30 50 70 Chickweed 98 100 95 98 90 100 10098 100 100 100 100 100 98 Cocklebur 98 100 95 70 100 95 98 98 90 100 100100 100 100 Corn 85 75 80 98 75 60 60 60 80 35 80 75 70 80 Crabgrass,Large 98 98 98 98 80 100 100 90 90 80 90 95 95 95 Cupgrass, Woolly 95 9095 75 55 98 70 70 70 65 85 75 95 85 Deadnettle — — — — — — — — — — — — —— Foxtail, Giant 98 95 95 98 85 98 98 85 98 85 85 90 85 95 Foxtail,Green 100 95 100 80 90 98 98 90 80 90 85 95 95 98 Galium — — — — — — — —— — — — — — Goosegrass 95 98 70 80 75 85 90 75 85 90 85 98 90 80Johnsongrass 100 45 100 100 65 100 100 70 45 45 80 85 98 95 Kochia 98100 85 100 98 95 100 98 90 100 100 100 98 100 Lambsquarters 100 100 100100 100 100 100 98 100 100 100 100 100 100 Morningglory 100 65 95 100100 98 100 100 100 100 100 100 100 100 Nutsedge, Yellow 85 75 75 75 7575 75 70 65 85 85 80 75 75 Oat, Wild 80 90 80 50 20 50 10 5 30 0 30 1050 80 Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100Ragweed 98 98 98 100 95 98 75 98 80 95 95 100 90 95 Ryegrass, Italian 6060 80 30 0 20 30 0 10 0 10 5 15 20 Soybean 98 100 98 98 100 98 98 98 9598 98 100 100 100 Surinam Grass 100 85 98 95 75 98 75 70 80 70 85 85 9080 Velvetleaf 100 100 98 100 100 100 100 98 80 100 100 100 98 100 Wheat45 50 5 10 35 50 0 5 5 0 15 5 20 5 Windgrass 95 95 70 50 50 65 90 55 500 45 85 70 60 Compounds 250 g ai/ha 100 102 107 108 109 111 113 117 118119 120 121 123 126 Postemergence Barley 50 60 30 0 5 30 20 0 0 5 5 1050 40 Bermudagrass 85 100 98 100 95 100 95 100 98 98 98 100 98 95Blackgrass 40 45 20 30 50 40 5 40 40 50 60 60 80 45 Bromegrass, Downy 3530 30 5 5 10 90 45 35 85 80 90 45 40 Canarygrass 10 50 80 5 45 15 90 515 30 55 30 85 90 Chickweed 100 100 100 100 100 100 100 100 100 100 100100 100 98 Cocklebur 98 100 100 100 100 100 98 100 98 95 80 100 100 98Corn 45 70 85 65 60 60 85 25 25 70 75 85 80 80 Crabgrass, Large 80 90 9585 85 85 95 95 95 95 98 98 90 90 Cupgrass, Woolly 75 85 80 75 75 75 9598 95 100 100 100 90 90 Deadnettle — — — — — — — — — — — — — — Foxtail,Giant 85 95 95 80 90 70 95 95 95 95 98 98 85 90 Foxtail, Green 85 95 9880 98 70 95 95 95 100 100 100 90 95 Galium — — — — — — — — — — — — — —Goosegrass 75 90 85 85 85 85 90 85 90 95 98 98 85 85 Johnsongrass 25 7590 60 75 40 95 25 35 80 80 85 90 90 Kochia 100 100 100 100 98 100 100 8598 100 98 100 100 85 Lambsquarters 98 100 100 100 100 100 98 100 100 100100 100 98 98 Morningglory 100 100 100 100 100 100 100 100 80 95 90 45100 100 Nutsedge, Yellow 40 80 85 85 80 85 75 35 65 75 75 50 80 80 Oat,Wild 30 80 40 0 40 10 85 35 40 95 95 98 60 50 Pigweed 98 98 100 100 100100 100 100 100 100 100 100 100 98 Ragweed 80 95 98 98 98 98 98 98 98 9880 95 98 90 Ryegrass, Italian 50 10 5 0 40 5 85 50 60 85 80 75 50 50Soybean 100 100 100 85 100 98 98 95 100 80 98 100 90 98 Surinam Grass 7585 85 80 80 80 90 85 90 98 100 100 85 98 Velvetleaf 85 100 100 100 100100 98 100 100 100 100 100 100 98 Wheat 35 30 15 5 15 30 50 25 10 60 8080 50 50 Windgrass 60 70 85 40 80 70 80 65 80 100 90 100 90 60 Compounds250 g ai/ha 127 128 129 130 140 141 146 147 152 155 156 157 160 162Postemergence Barley 60 5 0 0 0 5 30 0 90 85 85 30 50 85 Bermudagrass 98100 98 95 90 90 100 98 98 100 98 100 95 100 Blackgrass 40 15 5 5 5 25 5055 70 65 50 40 25 65 Bromegrass, Downy 40 50 35 40 20 45 35 10 85 50 4065 55 50 Canarygrass 60 30 0 25 5 5 10 5 85 65 60 90 35 90 Chickweed 98100 100 100 75 95 98 98 95 100 100 100 100 100 Cocklebur 100 100 100 10095 100 — 100 100 100 98 100 100 100 Corn 75 60 60 80 45 45 35 40 80 6560 100 60 85 Crabgrass, Large 95 100 85 100 90 85 98 90 95 90 80 100 9598 Cupgrass, Woolly 85 95 85 90 65 70 75 80 100 75 65 98 95 100Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 90 98 98 98 90 8598 90 98 95 90 100 85 98 Foxtail, Green 95 98 95 98 95 90 90 90 100 8085 95 98 100 Galium — — — — — — — — — — — — — — Goosegrass 85 98 95 9585 80 95 95 98 98 80 100 90 98 Johnsongrass 95 85 85 80 45 65 95 60 10070 65 100 75 100 Kochia 100 98 98 100 35 90 90 100 100 100 25 45 100 80Lambsquarters 95 100 98 100 80 100 100 100 100 100 100 100 98 100Morningglory 98 90 90 100 65 65 95 100 95 100 100 100 100 100 Nutsedge,Yellow 80 60 85 40 75 60 40 75 80 75 75 45 80 80 Oat, Wild 60 80 30 6040 40 70 45 85 70 50 70 60 55 Pigweed 100 100 98 100 98 98 100 100 100100 100 98 100 100 Ragweed 98 98 95 98 75 95 98 98 98 95 90 100 98 100Ryegrass, Italian 30 30 0 5 5 5 15 40 80 60 40 35 35 90 Soybean 98 98 98100 80 90 100 85 100 100 98 100 98 100 Surinam Grass 90 85 85 90 65 7575 75 95 75 70 100 75 85 Velvetleaf 100 100 100 100 85 98 100 100 100100 100 100 100 100 Wheat 40 5 0 10 15 10 45 10 90 70 45 30 45 40Windgrass 70 85 85 85 30 50 60 70 98 85 60 80 80 80 Compounds 250 gai/ha 164 173 181 184 186 187 189 190 191 193 197 217 218 219Postemergence Barley 35 50 55 60 5 40 40 70 70 50 40 10 35 30Bermudagrass 100 100 100 100 98 100 70 100 100 100 100 100 100 100Blackgrass 35 50 15 50 20 5 5 40 60 60 45 30 5 90 Bromegrass, Downy 9570 85 60 50 40 10 35 75 85 30 65 30 80 Canarygrass 98 80 90 95 40 60 1055 85 25 60 20 5 55 Chickweed 100 100 100 100 100 100 100 100 100 100100 100 100 100 Cocklebur 100 100 100 100 100 100 100 100 100 100 100100 — — Corn 70 85 95 98 65 80 45 65 85 60 65 35 80 80 Crabgrass, Large100 100 100 100 95 100 100 90 100 100 100 98 90 98 Cupgrass, Woolly 100100 100 100 85 95 80 85 98 98 98 55 80 98 Deadnettle — — — 100 100 100100 100 100 100 100 — — — Foxtail, Giant 100 100 100 100 95 100 98 95100 100 100 90 85 95 Foxtail, Green 100 90 98 98 95 98 95 70 98 80 70 9090 90 Galium — — — 60 70 85 85 85 60 90 80 — — — Goosegrass 98 100 100100 100 100 90 98 100 100 100 95 35 95 Johnsongrass 98 — 100 100 100 10070 80 100 80 100 65 80 100 Kochia 100 100 100 10 100 80 100 98 35 100 98100 100 100 Lambsquarters 100 100 100 100 100 100 100 100 100 100 100100 100 100 Morningglory 100 95 100 100 100 100 100 100 100 90 100 80 98100 Nutsedge, Yellow 75 75 85 75 80 75 65 75 70 75 75 70 60 85 Oat, Wild90 85 100 98 45 45 25 50 80 75 85 85 60 85 Pigweed 100 100 100 100 100100 100 100 100 100 100 100 100 100 Ragweed 100 98 100 — 100 100 80 — —— — 98 100 100 Ryegrass, Italian 40 30 65 60 30 30 5 30 50 45 35 40 7040 Soybean 100 100 100 100 100 100 100 98 100 100 100 98 100 100 SurinamGrass 98 — 100 100 — — 85 90 98 95 70 95 90 65 Velvetleaf 95 100 100 100100 100 100 100 100 100 100 100 100 98 Wheat 50 50 70 60 5 5 0 30 65 6040 50 0 50 Windgrass 85 75 65 100 65 80 80 65 100 75 98 85 45 85Compounds 250 g ai/ha 220 226 227 228 229 233 235 236 237 238 239 240243 244 Postemergence Barley 15 60 30 40 25 10 — 0 40 40 5 15 95 98Bermudagrass 100 98 90 95 90 100 100 — 100 100 100 100 100 100Blackgrass 40 60 20 55 30 50 — 40 80 70 50 65 98 85 Bromegrass, Downy 3030 25 10 30 60 85 25 95 85 10 50 100 80 Canarygrass 30 60 10 10 60 20 3010 50 30 0 40 100 100 Chickweed 100 95 90 100 98 100 100 100 100 100 100100 100 100 Cocklebur — 100 95 100 100 100 — 100 — — 100 — — — Corn 7598 85 90 85 85 100 — 100 95 75 100 100 100 Crabgrass, Large 90 98 90 9890 100 100 100 100 98 98 100 100 100 Cupgrass, Woolly 65 95 95 98 90 100100 — 100 100 95 100 100 100 Deadnettle — — — — — — — — — — — — — —Foxtail, Giant 95 95 98 95 95 98 100 98 100 100 98 100 98 100 Foxtail,Green 90 90 90 100 95 100 98 98 95 98 95 98 100 100 Galium — — — — — — —— — — — — — — Goosegrass 90 85 80 90 80 98 100 100 98 98 100 98 98 98Johnsongrass 90 100 65 100 100 25 100 55 100 100 — 100 100 100 Kochia100 100 100 100 100 — 100 100 100 100 98 100 100 100 Lambsquarters 10098 98 100 98 100 100 100 100 100 100 100 100 100 Morningglory 100 100100 100 100 100 100 — 100 100 100 — 100 100 Nutsedge, Yellow 55 75 65 7055 25 60 65 45 25 70 45 85 75 Oat, Wild 50 50 30 40 35 60 95 60 90 60 3060 100 98 Pigweed 100 98 100 100 100 — 100 — 100 100 100 100 100 100Ragweed 98 90 85 98 95 98 100 98 100 100 100 100 100 100 Ryegrass,Italian 60 20 10 0 10 60 60 5 60 70 0 40 95 95 Soybean 100 100 98 100 98100 100 100 100 100 98 100 100 100 Surinam Grass 75 85 95 98 90 100 100— 100 100 75 100 100 100 Velvetleaf 100 98 98 100 85 100 100 100 100 100100 100 100 100 Wheat 15 30 20 35 35 65 80 60 85 80 30 50 100 95Windgrass 60 85 50 90 65 60 98 85 100 95 70 98 100 95 Compounds 250 gai/ha 245 255 Postemergence Barley 95 50 Bermudagrass 100 100 Blackgrass80 60 Bromegrass, Downy 95 85 Canarygrass 100 60 Chickweed 100 100Cocklebur — — Corn 100 85 Crabgrass, Large 100 95 Cupgrass, Woolly 10098 Deadnettle — — Foxtail, Giant 100 100 Foxtail, Green 100 90 Galium —— Goosegrass 100 98 Johnsongrass 100 95 Kochia 100 65 Lambsquarters 100100 Morningglory 100 100 Nutsedge, Yellow 75 60 Oat, Wild 100 90 Pigweed100 100 Ragweed 100 95 Ryegrass, Italian 85 80 Soybean 100 100 SurinamGrass 100 90 Velvetleaf 100 100 Wheat 98 80 Windgrass 98 95 Compounds125 g ai/ha 1 2 3 4 7 8 9 10 11 12 14 24 26 27 Postemergence Barley 0 300 0 0 5 20 0 10 0 5 50 0 10 Bermudagrass 60 90 70 85 65 95 98 90 100 9880 100 60 100 Blackgrass 5 45 0 30 0 10 40 50 40 10 5 40 10 45Bromegrass, Downy 0 80 0 50 5 10 40 10 45 20 50 70 20 20 Canarygrass 080 0 75 0 70 50 5 90 5 20 — 50 30 Chickweed 65 95 98 100 90 100 95 95100 100 80 95 85 50 Cocklebur 70 95 85 100 65 100 35 95 100 100 90 98 9595 Corn 0 35 10 50 0 75 75 45 80 45 45 85 40 50 Crabgrass, Large 55 9080 100 45 90 85 75 100 80 85 95 50 60 Cupgrass, Woolly 0 85 20 100 50 9080 70 90 70 80 95 85 70 Deadnettle — — — — — — — — — — — — — — Foxtail,Giant 20 85 60 98 55 100 95 80 98 98 80 90 70 90 Foxtail, Green 30 10035 60 30 85 80 70 85 70 50 90 85 80 Galium — — — — — — — — — — — — — —Goosegrass 65 95 70 85 35 95 90 95 95 98 80 85 95 98 Johnsongrass 0 98 —95 0 98 85 60 90 60 80 70 50 45 Kochia 25 80 85 100 45 100 25 15 75 60 —80 — 100 Lambsquarters 90 95 98 100 65 100 80 90 95 98 85 90 90 95Morningglory 45 95 55 90 15 100 70 45 70 70 80 60 75 80 Nutsedge, Yellow20 75 65 75 0 80 60 60 50 65 30 30 35 50 Oat, Wild 10 55 5 50 0 35 40 2070 20 50 60 45 50 Pigweed 85 95 100 100 90 100 100 95 85 98 80 80 85 100Ragweed 70 90 98 100 80 100 75 90 100 100 85 90 98 100 Ryegrass, Italian0 40 5 15 0 30 30 0 40 5 5 40 10 5 Soybean 70 95 80 100 75 98 85 95 100100 90 95 95 95 Surinam Grass 10 85 40 75 20 75 75 70 85 65 50 60 60 80Velvetleaf 85 90 100 90 90 95 90 75 100 98 90 98 95 80 Wheat 0 20 10 5010 35 30 0 40 0 0 30 5 10 Windgrass 0 50 0 60 5 30 60 30 85 45 30 60 4050 Compounds 125 g ai/ha 29 33 34 36 37 38 39 40 42 44 45 46 47 48Postemergence Barley 0 0 30 20 0 0 0 10 0 5 5 0 10 10 Bermudagrass 90 9895 100 98 100 85 100 95 95 95 90 98 98 Blackgrass 40 30 10 15 5 15 0 1015 30 10 10 25 20 Bromegrass, Downy 40 10 50 45 15 85 0 70 15 80 45 1050 50 Canarygrass 40 5 50 50 10 10 0 30 0 30 30 0 40 45 Chickweed 50 10098 100 85 100 100 100 80 98 98 95 100 95 Cocklebur 95 95 85 — — — 95 —85 90 70 80 95 98 Corn 50 10 45 65 60 75 45 85 20 80 60 60 80 85Crabgrass, Large 55 90 95 95 85 98 85 100 85 95 75 75 90 95 Cupgrass,Woolly 85 70 90 95 75 95 85 98 25 85 75 25 90 90 Deadnettle — — — — — —— — — — — — — — Foxtail, Giant 90 85 95 98 95 100 95 100 75 95 95 80 9895 Foxtail, Green 75 90 90 90 85 95 90 95 60 90 85 85 95 95 Galium — — —— — — — — — — — — — — Goosegrass 85 85 90 90 85 90 65 95 90 90 80 80 9595 Johnsongrass 40 35 95 85 60 95 90 75 40 90 98 70 98 80 Kochia — 95100 60 15 100 60 10 100 75 15 20 98 100 Lambsquarters 90 98 100 100 98100 100 100 100 95 100 90 98 100 Morningglory 80 80 85 75 75 75 75 75 7575 80 45 90 80 Nutsedge, Yellow 70 75 55 25 25 15 15 55 70 50 45 70 7060 Oat, Wild 60 40 60 75 40 80 30 90 10 80 60 20 60 85 Pigweed 80 98 9890 98 98 100 100 100 98 100 80 100 100 Ragweed 100 98 95 95 95 80 95 9885 95 95 80 95 90 Ryegrass, Italian 40 40 20 10 5 60 5 0 10 10 35 5 3030 Soybean 98 98 95 100 95 90 98 100 95 95 98 90 98 98 Surinam Grass 7075 80 85 75 90 65 98 45 95 95 80 98 95 Velvetleaf 80 98 98 100 95 100 80100 95 100 90 85 98 98 Wheat 10 5 35 5 0 40 5 30 5 30 15 0 5 10Windgrass 30 30 50 80 50 85 5 80 70 85 70 15 80 90 Compounds 125 g ai/ha49 50 51 52 53 55 56 58 59 61 62 63 64 66 Postemergence Barley 0 5 30 2570 0 30 5 10 0 5 0 — 0 Bermudagrass 95 100 90 95 98 85 100 98 98 90 8585 98 95 Blackgrass 0 5 50 25 40 5 20 20 40 0 30 35 5 10 Bromegrass,Downy 0 20 55 60 55 0 50 45 35 0 50 20 60 20 Canarygrass 0 5 60 65 90 040 80 50 0 0 0 40 0 Chickweed 80 98 85 95 98 80 98 90 98 95 75 80 98 95Cocklebur 80 90 90 85 85 65 75 85 90 70 55 90 95 25 Corn 5 25 80 65 80 565 65 75 10 75 25 85 70 Crabgrass, Large 80 95 85 90 95 80 90 90 95 7580 80 98 65 Cupgrass, Woolly 55 80 80 85 95 15 65 70 90 60 60 65 98 60Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 70 95 85 90 90 5585 90 95 65 75 65 98 80 Foxtail, Green 75 95 95 98 100 80 98 98 70 60 8070 100 90 Galium — — — — — — — — — — — — — — Goosegrass 70 90 85 85 8065 75 85 95 65 65 70 85 70 Johnsongrass 10 65 85 90 95 10 85 98 100 10 010 100 65 Kochia 80 100 25 55 75 75 100 25 45 70 60 25 80 90Lambsquarters 90 100 95 90 98 95 100 100 100 95 98 98 100 95Morningglory 80 70 90 75 80 75 100 90 80 70 75 75 85 100 Nutsedge,Yellow 70 70 75 45 75 55 75 55 70 60 35 50 10 65 Oat, Wild 5 10 60 95 850 40 60 55 0 25 5 95 5 Pigweed 95 100 98 95 100 90 100 98 100 90 100 95100 100 Ragweed 80 98 90 80 95 95 75 90 90 85 75 80 90 25 Ryegrass,Italian 0 0 10 55 40 0 50 30 70 0 50 0 0 5 Soybean 85 95 95 95 95 60 9595 95 10 90 85 98 98 Surinam Grass 55 80 90 90 98 45 85 95 90 75 65 3598 85 Velvetleaf 98 98 90 98 95 98 98 85 95 95 95 98 98 98 Wheat 15 5 1035 30 5 0 0 10 0 5 0 30 0 Windgrass 5 60 60 90 85 0 60 60 60 0 35 40 9570 Compounds 125 g ai/ha 67 68 69 70 71 72 73 74 75 77 79 80 81 82Postemergence Barley 20 25 15 90 0 0 0 0 0 0 35 30 0 0 Bermudagrass 7095 98 95 80 85 90 95 98 95 85 45 95 85 Blackgrass 5 0 0 35 0 0 10 25 0 030 5 30 5 Bromegrass, Downy 0 25 70 70 10 0 50 5 35 5 30 60 30 5Canarygrass 0 35 25 85 5 0 5 0 0 0 35 50 10 15 Chickweed 95 98 98 98 9590 95 95 98 95 95 100 98 98 Cocklebur 90 90 20 40 95 90 65 90 95 60 9845 65 95 Corn 65 80 25 60 0 5 80 15 20 60 60 65 15 5 Crabgrass, Large 9090 98 95 80 85 90 95 100 75 90 90 95 80 Cupgrass, Woolly 70 55 95 90 8550 65 55 55 35 65 70 90 65 Deadnettle — — — — — — — — — — — — — —Foxtail, Giant 85 85 98 95 80 75 80 70 85 75 95 95 95 95 Foxtail, Green80 85 100 98 70 90 90 80 90 80 80 95 95 85 Galium — — — — — — — — — — —— — — Goosegrass 65 85 85 85 90 65 75 80 95 75 70 80 70 80 Johnsongrass5 75 100 80 98 40 70 10 20 10 70 10 75 80 Kochia 85 95 80 75 25 90 90 95100 95 75 20 90 65 Lambsquarters 98 100 100 100 90 100 100 95 100 98 10098 100 100 Morningglory 95 98 75 100 75 90 75 95 95 80 100 100 100 100Nutsedge, Yellow 65 70 40 40 10 65 50 70 70 70 70 55 80 45 Oat, Wild 1050 85 90 0 30 80 60 50 5 60 40 50 5 Pigweed 98 100 100 98 98 100 100 100100 100 100 100 100 100 Ragweed 85 80 100 75 80 90 85 85 90 80 95 65 9895 Ryegrass, Italian 5 15 50 50 0 10 60 20 40 5 50 5 45 5 Soybean 98 9898 95 95 85 90 95 98 70 95 90 95 95 Surinam Grass 20 70 100 95 65 80 8565 70 75 75 60 98 75 Velvetleaf 98 100 98 100 90 100 100 100 100 98 98100 100 90 Wheat 25 5 10 35 0 10 40 30 10 10 35 20 25 0 Windgrass 5 6580 90 45 60 90 80 70 20 65 70 60 20 Compounds 125 g ai/ha 83 85 86 87 8889 90 91 92 93 94 95 96 97 Postemergence Barley 5 20 60 0 40 10 10 30 05 5 0 0 0 Bermudagrass 85 90 95 98 80 95 85 95 85 85 98 75 95 95Blackgrass 0 35 45 20 5 20 5 30 5 30 10 0 30 30 Bromegrass, Downy 45 2535 60 45 5 10 5 20 0 0 0 5 5 Canarygrass 25 55 80 35 80 50 30 65 0 5 300 30 10 Chickweed 98 95 95 100 95 98 85 98 98 95 100 98 98 100 Cocklebur80 98 95 100 95 65 100 95 98 95 60 100 98 100 Corn 15 85 80 75 65 98 4545 45 50 70 25 65 60 Crabgrass, Large 95 90 98 95 98 95 75 98 98 80 9075 85 85 Cupgrass, Woolly 90 90 95 75 90 65 50 98 65 65 65 65 85 70Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 95 90 98 85 95 9075 98 90 80 85 75 80 85 Foxtail, Green 98 95 100 90 100 70 80 98 98 8070 65 70 85 Galium — — — — — — — — — — — — — — Goosegrass 80 80 85 95 7075 75 85 75 65 75 75 85 80 Johnsongrass 100 95 100 35 100 100 30 95 9850 45 15 70 75 Kochia 80 85 98 100 80 85 85 85 95 95 80 100 95 98Lambsquarters 100 98 100 100 100 98 100 100 100 95 100 98 100 100Morningglory 85 100 90 65 95 90 100 98 100 95 100 100 100 100 Nutsedge,Yellow 70 85 75 70 70 70 70 75 70 70 60 85 85 80 Oat, Wild 10 25 60 6570 20 10 45 5 0 5 0 25 5 Pigweed 100 100 100 — 100 100 100 100 100 98100 100 98 100 Ragweed 85 85 95 98 95 95 85 95 75 85 65 95 95 100Ryegrass, Italian 0 35 50 40 30 20 0 10 5 0 0 0 10 0 Soybean 90 90 98100 98 98 98 95 98 95 95 98 75 95 Surinam Grass 85 85 98 — 95 80 70 9870 70 65 45 75 80 Velvetleaf 95 98 100 100 95 98 100 100 100 95 75 10098 100 Wheat 0 20 40 50 5 5 15 35 0 0 0 0 10 0 Windgrass 15 80 85 85 6530 5 50 80 50 45 0 45 60 Compounds 125 g ai/ha 98 99 100 102 107 108 109111 113 117 118 119 120 121 Postemergence Barley 10 10 30 30 25 0 5 5 50 0 5 5 5 Bermudagrass 85 80 75 85 95 100 90 100 95 95 98 98 98 100Blackgrass 20 5 10 30 15 20 40 25 5 40 35 50 60 40 Bromegrass, Downy 525 15 10 10 5 5 5 80 15 30 60 60 80 Canarygrass 35 60 5 30 60 5 30 0 — 510 30 55 5 Chickweed 98 98 95 95 100 100 98 100 100 98 95 100 85 100Cocklebur 100 100 95 100 100 100 100 100 98 98 85 80 25 85 Corn 55 65 2065 75 50 60 55 80 25 20 60 50 55 Crabgrass, Large 80 95 75 85 90 75 7580 95 95 80 95 95 95 Cupgrass, Woolly 75 80 70 75 75 70 60 75 95 95 7598 100 100 Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 85 9580 80 85 75 80 65 90 80 85 95 85 98 Foxtail, Green 85 95 80 90 90 80 8565 80 80 95 95 95 100 Galium — — — — — — — — — — — — — — Goosegrass 8075 75 80 75 75 80 85 85 75 80 85 85 98 Johnsongrass 75 80 10 60 70 20 5020 90 — 20 75 75 — Kochia 80 100 98 100 100 98 85 100 100 — 70 95 80 —Lambsquarters 100 100 98 100 100 100 100 100 98 100 100 100 98 100Morningglory 100 100 100 100 100 100 100 100 100 80 70 95 80 25Nutsedge, Yellow 70 70 15 75 75 80 75 80 75 25 65 65 65 45 Oat, Wild 2040 30 40 20 0 30 0 45 30 10 95 80 98 Pigweed 100 100 98 95 100 100 100100 100 — 100 100 100 100 Ragweed 80 80 75 85 95 95 95 98 98 90 95 95 7590 Ryegrass, Italian 15 20 10 5 5 0 5 0 50 15 5 60 60 70 Soybean 98 100100 95 100 65 98 95 98 95 95 60 95 95 Surinam Grass 85 75 65 75 80 65 6570 90 — 75 95 100 100 Velvetleaf 95 100 70 100 100 100 100 100 98 95 98100 98 100 Wheat 5 5 15 20 5 0 5 5 40 20 5 60 60 45 Windgrass 50 10 4560 80 30 60 35 35 65 70 100 90 100 Compounds 125 g ai/ha 122 123 126 127128 129 130 131 140 141 146 147 152 155 Postemergence Barley 50 25 15 350 0 0 0 0 5 15 0 85 45 Bermudagrass 85 90 90 98 98 95 90 85 85 85 100 9598 98 Blackgrass 15 40 30 25 10 5 5 0 5 10 35 45 55 60 Bromegrass, Downy50 10 30 20 40 15 35 0 5 10 10 5 60 35 Canarygrass 45 55 60 35 30 0 20 05 5 5 5 80 50 Chickweed 80 95 98 98 95 90 100 90 45 90 98 98 90 100Cocklebur 85 100 80 95 100 98 95 100 65 95 — 90 98 98 Corn 25 75 55 2560 60 80 20 25 45 20 25 65 40 Crabgrass, Large 85 85 85 90 95 85 95 8080 80 85 85 95 80 Cupgrass, Woolly 75 75 85 85 90 85 85 65 65 65 65 8098 65 Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 80 80 85 8598 90 98 80 80 80 95 85 95 90 Foxtail, Green 85 85 90 90 95 90 95 95 8590 80 80 98 80 Galium — — — — — — — — — — — — — — Goosegrass 70 80 75 7598 90 95 75 70 75 95 80 95 85 Johnsongrass 75 75 85 80 85 70 80 50 35 5070 60 95 65 Kochia 45 80 25 100 95 95 100 75 10 85 85 80 95 100Lambsquarters 90 98 85 90 100 95 100 98 75 98 100 98 98 100 Morningglory85 100 100 90 90 90 100 75 65 60 85 65 75 100 Nutsedge, Yellow 75 75 8075 60 60 35 45 65 60 20 70 80 70 Oat, Wild 35 30 35 25 60 20 40 0 10 1550 20 80 60 Pigweed 98 100 98 95 98 98 100 100 75 95 100 100 100 100Ragweed 75 95 85 98 95 95 98 95 65 85 98 90 95 90 Ryegrass, Italian 40 55 5 5 0 0 0 0 0 10 30 45 40 Soybean 80 85 85 98 98 98 98 98 75 75 98 6598 100 Surinam Grass 90 85 85 85 85 85 80 65 55 70 75 75 90 65Velvetleaf 98 95 95 100 95 95 98 98 80 98 98 95 100 100 Wheat 50 15 3525 0 0 5 0 10 5 15 5 85 40 Windgrass 50 80 40 55 70 80 75 5 5 40 60 5585 70 Compounds 125 g ai/ha 156 157 160 162 164 169 173 181 184 186 187189 190 191 Postemergence Barley 60 30 35 50 30 0 35 50 60 5 40 15 40 50Bermudagrass 95 100 90 100 98 100 100 100 100 95 100 65 100 100Blackgrass 35 10 20 55 10 10 30 15 40 5 5 5 35 50 Bromegrass, Downy 3560 50 45 85 90 40 60 50 30 35 5 35 50 Canarygrass 40 80 20 90 90 80 4085 80 40 55 5 25 60 Chickweed 100 100 95 100 98 100 100 100 100 100 100100 100 98 Cocklebur 75 100 100 100 100 100 100 100 100 100 100 100 9598 Corn 45 95 50 80 45 55 60 95 85 30 75 35 40 75 Crabgrass, Large 65 9895 98 98 100 95 100 100 85 100 95 80 100 Cupgrass, Woolly 55 98 85 10098 100 100 100 100 80 85 75 80 90 Deadnettle — — — — — — — — 100 100 —100 100 100 Foxtail, Giant 85 100 75 98 98 100 100 100 100 95 100 90 90100 Foxtail, Green 85 85 70 98 98 95 90 95 85 85 98 90 45 80 Galium — —— — — — — — 60 70 55 85 60 60 Goosegrass 70 98 90 90 98 100 95 100 10098 100 90 80 100 Johnsongrass 45 100 65 100 95 65 95 100 100 75 100 6575 100 Kochia 20 10 100 75 100 100 98 100 5 100 70 98 98 25Lambsquarters 95 100 98 98 100 100 100 100 100 100 100 100 100 98Morningglory 100 95 100 90 98 100 80 100 100 100 100 100 85 90 Nutsedge,Yellow 70 40 80 75 70 55 60 80 45 75 65 55 65 55 Oat, Wild 35 60 50 4585 85 70 90 80 20 45 10 40 70 Pigweed 98 90 100 100 100 100 100 100 75100 100 100 100 98 Ragweed 75 100 98 100 98 100 90 100 — 100 100 75 — —Ryegrass, Italian 20 30 35 80 20 10 30 60 45 0 10 5 20 50 Soybean 98 10098 100 100 95 95 100 100 100 100 98 95 100 Surinam Grass 60 98 60 75 95— — 95 100 — — 80 75 90 Velvetleaf 95 100 100 95 80 100 100 100 100 100100 100 100 90 Wheat 35 20 40 35 35 5 40 50 55 0 5 0 30 55 Windgrass 5570 60 60 75 55 70 60 90 50 65 60 65 85 Compounds 125 g ai/ha 193 197 217218 219 220 225 226 227 228 229 233 235 236 Postemergence Barley 50 1010 35 30 10 40 30 5 40 5 10 40 0 Bermudagrass 100 100 98 95 100 98 85 8585 90 85 100 100 98 Blackgrass 40 10 30 5 55 30 15 40 5 50 5 30 70 30Bromegrass, Downy 40 30 40 20 80 15 85 5 0 10 20 50 50 10 Canarygrass 2540 20 0 55 10 85 50 5 5 50 10 30 0 Chickweed 100 100 100 100 100 98 9585 80 100 90 100 100 100 Cocklebur 100 100 98 — — — 100 100 95 100 100100 — 100 Corn 40 45 25 75 75 55 70 98 75 85 85 85 100 70 Crabgrass,Large 98 98 90 70 95 85 95 95 85 98 90 98 98 98 Cupgrass, Woolly 95 9045 60 95 65 85 85 90 95 80 100 100 95 Deadnettle 100 100 — — — — — — — —— — — — Foxtail, Giant 95 98 85 65 80 55 85 95 90 95 80 98 100 95Foxtail, Green 60 50 85 90 90 80 98 90 90 98 80 95 95 98 Galium 90 — — —— — — — — — — — — — Goosegrass 98 100 85 15 95 85 95 85 75 85 70 98 9895 Johnsongrass 70 95 60 55 98 80 75 100 60 95 100 25 100 20 Kochia 10095 100 100 98 75 15 100 85 100 80 — 100 100 Lambsquarters 98 100 100 100100 100 98 95 98 100 95 100 100 100 Morningglory 65 100 80 80 100 98 95100 100 100 100 98 100 95 Nutsedge, Yellow 75 65 70 15 70 25 25 70 65 6040 25 55 15 Oat, Wild 70 70 50 60 80 30 85 50 10 15 10 45 85 20 Pigweed100 98 100 100 100 100 98 98 100 100 95 — 100 98 Ragweed — — 85 98 98 9890 85 70 95 80 98 100 98 Ryegrass, Italian 40 30 40 60 40 30 40 5 5 0 050 55 0 Soybean 98 100 95 100 100 90 98 100 95 100 98 100 100 98 SurinamGrass 80 65 80 85 35 60 85 80 80 95 80 100 100 75 Velvetleaf 100 100 100100 95 95 90 90 98 100 85 95 100 100 Wheat 60 5 50 0 50 0 55 25 10 20 560 80 30 Windgrass 70 50 80 45 60 40 80 70 40 80 50 60 95 70 Compounds125 g ai/ha 237 238 239 240 243 244 245 255 Postemergence Barley 40 35 515 95 90 85 35 Bermudagrass 100 100 100 100 100 100 100 95 Blackgrass 7060 30 65 85 65 80 10 Bromegrass, Downy 90 50 5 25 95 75 95 80Canarygrass 50 30 0 30 100 98 100 50 Chickweed 100 100 98 100 100 98 100100 Cocklebur — — 100 — — — — — Corn 100 95 45 100 100 95 100 85Crabgrass, Large 100 98 95 100 100 100 100 90 Cupgrass, Woolly 100 10095 100 100 100 100 95 Deadnettle — — — — — — — — Foxtail, Giant 98 10090 100 98 95 100 98 Foxtail, Green 95 98 90 95 100 98 100 90 Galium — —— — — — — — Goosegrass 98 98 98 98 98 98 100 95 Johnsongrass 100 98 60100 100 100 100 90 Kochia 100 100 98 100 100 100 100 15 Lambsquarters100 100 100 100 100 100 100 98 Morningglory 100 100 100 — 100 100 100 85Nutsedge, Yellow 45 20 65 20 70 65 70 15 Oat, Wild 60 50 5 45 85 95 8585 Pigweed 100 100 98 100 100 100 100 98 Ragweed 100 100 100 100 98 98100 95 Ryegrass, Italian 60 25 0 40 85 80 70 30 Soybean 100 100 98 95100 100 100 100 Surinam Grass 100 100 45 100 100 100 100 90 Velvetleaf100 100 100 85 100 100 100 98 Wheat 85 80 5 50 95 85 95 50 Windgrass 9885 30 98 98 80 95 80 Compounds 62 g ai/ha 1 2 3 4 7 8 9 10 11 12 14 2426 27 Postemergence Barley 0 20 0 0 0 0 0 0 10 0 0 5 0 0 Bermudagrass 5085 25 85 45 85 95 75 100 85 70 95 50 90 Blackgrass 0 30 0 20 0 10 0 0 510 0 10 0 5 Bromegrass, Downy 0 60 0 15 0 5 30 0 35 10 30 50 15 5Canarygrass 0 50 0 20 0 50 25 0 50 5 20 40 30 10 Chickweed 60 90 98 10080 100 85 95 98 100 — 90 50 45 Cocklebur 65 90 80 100 45 100 0 90 100 9890 98 80 95 Corn 0 25 0 25 0 65 45 15 75 30 40 50 35 40 Crabgrass, Large50 85 70 85 45 85 80 70 85 75 55 75 50 50 Cupgrass, Woolly 0 80 15 95 5080 75 70 75 60 80 80 40 60 Deadnettle — — — — — — — — — — — — — —Foxtail, Giant 15 85 45 98 55 100 85 75 85 90 70 85 60 85 Foxtail, Green10 90 10 40 20 70 40 25 60 60 45 40 40 80 Galium — — — — — — — — — — — —— — Goosegrass 60 90 50 75 25 85 85 75 85 85 80 85 90 90 Johnsongrass 090 0 80 0 98 70 55 70 60 80 60 50 45 Kochia 20 75 80 100 45 100 15 15 2520 — 70 — — Lambsquarters 75 90 95 100 65 100 80 80 70 85 85 90 90 95Morningglory 20 80 20 85 15 90 45 45 15 60 70 60 50 80 Nutsedge, Yellow20 60 45 65 0 70 25 55 35 55 30 30 30 40 Oat, Wild 5 45 0 50 0 15 5 5 505 40 50 40 50 Pigweed 80 90 90 100 75 100 85 85 80 95 80 80 80 98Ragweed 70 80 85 100 65 100 75 80 100 100 80 80 85 98 Ryegrass, Italian0 40 0 10 0 20 0 0 10 0 5 5 0 5 Soybean 65 90 70 100 65 98 75 95 100 10085 95 95 95 Surinam Grass 0 75 25 70 10 65 65 70 70 55 50 55 40 70Velvetleaf 75 85 100 75 80 80 85 70 95 85 90 90 70 60 Wheat 0 10 0 5 030 5 0 35 0 0 10 0 5 Windgrass 0 15 0 55 5 20 55 10 85 40 30 30 30 10Compounds 62 g ai/ha 29 33 34 36 37 38 39 40 42 44 45 46 47 48Postemergence Barley 0 0 30 10 0 0 0 0 0 0 5 0 10 5 Bermudagrass 90 9595 98 90 100 60 100 75 95 85 85 — 95 Blackgrass 20 15 5 5 0 15 0 10 1010 5 5 20 5 Bromegrass, Downy 10 5 50 30 10 70 0 50 5 70 20 5 40 25Canarygrass 20 0 50 45 5 10 0 20 0 20 10 0 30 30 Chickweed 50 98 75 9880 90 100 100 70 95 85 95 98 90 Cocklebur 95 90 25 — — — 75 — 45 80 5080 — 95 Corn 35 10 0 55 15 70 45 80 10 80 45 35 — 70 Crabgrass, Large 5085 85 95 75 90 80 98 75 90 75 65 85 85 Cupgrass, Woolly 85 65 80 90 6590 85 95 20 80 75 20 90 80 Deadnettle — — — — — — — — — — — — — —Foxtail, Giant 90 80 90 95 85 98 85 100 65 95 90 80 98 85 Foxtail, Green75 85 90 90 65 90 80 95 55 90 80 60 90 95 Galium — — — — — — — — — — — —— — Goosegrass 85 75 80 85 85 85 55 90 85 90 75 75 95 85 Johnsongrass 2035 90 75 40 75 65 — 0 70 90 50 — 80 Kochia — 80 95 0 0 80 45 0 100 75 00 95 98 Lambsquarters 85 98 98 100 98 95 95 100 95 95 98 85 98 95Morningglory 70 60 80 70 70 70 75 — 70 70 75 30 80 70 Nutsedge, Yellow50 50 25 20 15 0 0 35 60 50 10 70 65 45 Oat, Wild 50 15 50 75 10 75 2085 10 80 55 5 60 50 Pigweed 65 95 90 85 85 98 100 98 95 95 98 75 98 85Ragweed 85 95 85 90 80 80 85 98 75 95 85 75 90 85 Ryegrass, Italian 2010 10 5 0 50 5 0 5 5 30 5 30 5 Soybean 95 98 95 98 80 85 95 100 90 95 9580 95 95 Surinam Grass 50 65 75 85 70 85 65 95 40 95 75 75 95 85Velvetleaf 55 90 95 100 80 100 80 100 80 98 80 80 85 85 Wheat 0 0 10 5 020 5 20 0 10 15 0 0 0 Windgrass 10 25 40 70 30 80 0 70 60 70 60 10 — 80Compounds 62 g ai/ha 49 50 51 52 53 55 56 58 59 61 62 63 64 66Postemergence Barley 0 0 25 0 50 0 10 5 0 0 5 0 — 0 Bermudagrass 85 10090 95 95 80 85 85 90 90 80 85 95 70 Blackgrass 0 5 30 5 30 0 10 10 35 030 35 0 10 Bromegrass, Downy 0 5 50 55 50 0 45 40 30 0 45 20 45 10Canarygrass 0 0 60 50 80 0 30 60 5 0 0 0 40 0 Chickweed 75 80 80 95 9875 95 80 98 80 70 65 98 85 Cocklebur 80 85 85 85 85 60 55 85 85 65 55 8095 10 Corn 5 10 80 45 80 5 65 45 0 0 70 20 85 55 Crabgrass, Large 75 8585 90 95 75 85 80 85 65 75 75 90 55 Cupgrass, Woolly 50 75 75 75 90 1045 65 75 55 55 60 95 40 Deadnettle — — — — — — — — — — — — — — Foxtail,Giant 60 85 80 80 85 30 80 85 90 65 65 65 95 75 Foxtail, Green 50 80 9598 100 40 85 90 70 55 70 70 85 85 Galium — — — — — — — — — — — — — —Goosegrass 70 80 80 80 80 60 75 75 80 50 65 70 80 65 Johnsongrass 0 1075 85 95 0 80 85 75 0 0 10 98 60 Kochia 65 100 20 25 65 65 95 10 10 2525 25 55 85 Lambsquarters 80 98 90 85 95 80 98 95 98 95 95 95 100 95Morningglory 80 25 80 45 75 60 — 80 50 70 15 70 80 100 Nutsedge, Yellow65 70 65 25 65 10 70 40 60 60 25 20 10 45 Oat, Wild 5 5 60 90 70 0 20 6040 0 10 0 90 0 Pigweed 90 98 95 90 95 85 98 95 100 85 98 95 100 98Ragweed 80 90 80 80 85 80 55 85 80 80 75 75 85 10 Ryegrass, Italian 0 00 45 5 0 0 0 50 0 5 0 0 0 Soybean 65 85 90 95 95 60 85 85 95 0 80 75 9895 Surinam Grass 30 75 85 85 95 15 80 80 80 65 45 25 95 70 Velvetleaf 9598 85 98 85 98 90 75 90 80 95 98 98 90 Wheat 5 5 10 25 25 0 0 0 5 0 0 015 — Windgrass 0 50 60 80 80 0 40 50 60 0 35 30 90 60 Compounds 62 gai/ha 67 68 69 70 71 72 73 74 75 77 79 80 81 82 Postemergence Barley 5 05 30 0 0 0 0 0 0 30 30 0 0 Bermudagrass 70 75 98 85 75 80 80 80 98 90 8040 85 85 Blackgrass 0 0 0 35 0 0 10 0 0 0 15 0 10 0 Bromegrass, Downy 05 55 50 5 0 45 5 20 5 10 60 5 0 Canarygrass 0 0 0 80 5 0 0 0 0 0 30 50 50 Chickweed 95 90 98 90 90 85 80 85 90 85 95 98 98 90 Cocklebur 75 75 00 65 80 45 85 80 0 98 10 55 90 Corn 10 15 10 35 0 0 80 0 0 5 45 35 10 5Crabgrass, Large 80 90 95 90 75 80 85 80 98 60 85 80 95 75 Cupgrass,Woolly 70 10 95 65 45 45 65 10 55 20 40 70 75 55 Deadnettle — — — — — —— — — — — — — — Foxtail, Giant 80 80 98 85 75 70 75 55 80 75 75 90 85 80Foxtail, Green 80 85 98 85 60 70 90 20 85 80 60 95 85 60 Galium — — — —— — — — — — — — — — Goosegrass 55 70 80 85 75 65 75 75 80 75 65 75 70 75Johnsongrass 0 10 100 70 75 10 65 0 10 0 65 0 10 80 Kochia 80 90 70 65 085 80 75 95 80 75 20 80 60 Lambsquarters 95 98 100 98 85 100 98 95 10098 98 95 98 95 Morningglory 90 85 70 100 65 85 50 85 90 75 95 100 90 100Nutsedge, Yellow 65 10 10 15 10 65 20 20 65 60 60 15 80 15 Oat, Wild 520 80 70 0 — 80 20 20 5 45 30 35 0 Pigweed 98 95 100 98 85 100 98 98 10098 100 100 100 98 Ragweed 80 80 90 70 80 80 80 75 85 75 85 60 80 80Ryegrass, Italian 5 5 50 10 0 0 45 20 15 5 20 0 5 0 Soybean 90 95 90 7570 80 85 75 95 50 90 80 95 90 Surinam Grass 20 55 90 65 55 80 85 45 5065 45 45 90 65 Velvetleaf 95 100 98 80 85 100 100 100 100 98 98 100 10090 Wheat 5 5 5 20 0 5 35 5 0 5 25 10 20 0 Windgrass 0 50 60 85 10 20 8060 50 10 65 60 50 5 Compounds 62 g ai/ha 83 85 86 87 88 89 90 91 92 9394 95 96 97 Postemergence Barley 5 10 40 0 30 5 5 30 0 0 0 0 0 0Bermudagrass 75 85 90 90 80 85 80 95 80 75 80 75 95 95 Blackgrass 0 3530 5 5 15 5 20 0 5 10 0 20 20 Bromegrass, Downy 45 5 10 50 45 0 5 5 5 00 0 0 0 Canarygrass 20 40 20 30 70 35 10 55 0 0 5 0 5 10 Chickweed 90 9595 100 85 80 80 95 95 80 100 85 95 100 Cocklebur 80 95 95 100 90 60 9065 80 90 45 95 95 100 Corn 5 70 60 55 65 95 25 35 35 45 55 0 60 40Crabgrass, Large 85 90 98 85 98 95 75 95 90 80 75 65 80 80 Cupgrass,Woolly 85 85 85 75 80 50 45 85 25 45 65 55 75 60 Deadnettle — — — — — —— — — — — — — — Foxtail, Giant 95 80 95 80 95 85 70 98 75 80 75 65 70 75Foxtail, Green 95 95 95 80 98 70 65 85 80 60 60 50 65 85 Galium — — — —— — — — — — — — — — Goosegrass 80 70 75 80 70 65 60 75 70 65 70 75 70 70Johnsongrass 100 95 98 25 100 90 25 90 85 10 15 10 45 55 Kochia 75 85 85100 75 75 85 80 90 85 55 100 85 90 Lambsquarters 98 98 100 98 98 98 95100 98 95 95 98 98 100 Morningglory 75 100 80 45 90 85 95 90 95 80 75100 95 100 Nutsedge, Yellow 20 85 70 60 65 55 65 65 65 60 20 75 70 75Oat, Wild 10 25 50 60 55 10 5 30 5 0 5 0 5 5 Pigweed 90 100 100 98 10098 98 100 100 95 100 98 95 100 Ragweed 80 85 90 95 80 85 75 85 60 75 4580 80 98 Ryegrass, Italian 0 10 30 10 5 5 0 5 0 0 0 0 5 0 Soybean 90 8595 98 90 90 98 85 98 80 80 98 75 80 Surinam Grass 75 85 95 75 95 75 6598 65 65 60 45 75 75 Velvetleaf 90 98 100 100 90 95 98 100 100 90 70 9598 100 Wheat 0 5 35 35 5 5 10 10 0 0 0 0 5 0 Windgrass 10 70 60 60 60 55 40 50 10 40 0 10 50 Compounds 62 g ai/ha 98 99 100 102 107 108 109 111113 117 118 119 120 121 Postemergence Barley 5 5 20 10 5 0 0 0 5 0 0 0 55 Bermudagrass 80 75 70 85 80 90 85 100 90 90 95 98 95 98 Blackgrass 5 05 5 5 5 5 5 0 10 10 20 30 40 Bromegrass, Downy 5 5 10 10 5 0 0 0 60 10 530 60 50 Canarygrass 20 60 5 20 15 5 0 0 90 0 0 5 30 5 Chickweed 80 9875 80 100 100 98 100 98 95 95 80 75 100 Cocklebur 100 100 85 95 100 9598 98 95 75 40 10 15 45 Corn 35 65 10 15 65 35 15 45 60 15 0 45 20 55Crabgrass, Large 75 85 60 80 85 70 75 75 90 80 75 85 85 90 Cupgrass,Woolly 70 75 65 75 65 60 60 50 85 85 70 98 75 100 Deadnettle — — — — — —— — — — — — — — Foxtail, Giant 75 80 75 75 80 60 75 65 85 75 80 85 80 98Foxtail, Green 85 90 70 90 75 30 80 60 80 70 85 90 95 90 Galium — — — —— — — — — — — — — — Goosegrass 75 75 70 70 75 70 75 70 75 75 65 75 80 98Johnsongrass 70 75 5 25 70 20 30 15 85 20 10 40 25 70 Kochia 70 80 95 7098 95 75 100 100 50 65 75 40 100 Lambsquarters 98 100 98 98 100 98 98 9898 98 98 100 85 100 Morningglory 85 100 100 100 100 90 98 100 100 75 6060 50 20 Nutsedge, Yellow 60 70 5 65 75 75 65 75 75 0 45 50 35 45 Oat,Wild 20 20 10 15 5 0 0 0 40 10 5 60 80 90 Pigweed 100 100 98 70 100 98100 100 100 98 100 98 98 100 Ragweed 75 80 70 80 85 85 95 95 95 75 85 7575 85 Ryegrass, Italian 5 0 5 0 0 0 0 0 45 10 5 30 40 40 Soybean 98 10098 85 98 55 95 80 98 80 90 50 80 90 Surinam Grass 75 70 65 75 75 60 65 —85 75 — 85 85 100 Velvetleaf 95 100 70 100 100 100 98 98 95 85 75 80 9598 Wheat 5 5 5 10 5 0 5 0 15 5 5 40 40 45 Windgrass 20 5 40 10 40 10 4030 30 45 60 85 80 98 Compounds 62 g ai/ha 122 123 126 127 128 129 130131 140 141 146 147 152 155 Postemergence Barley 10 10 5 20 0 0 0 0 0 00 0 45 30 Bermudagrass 80 85 85 95 85 80 90 75 75 85 90 90 95 98Blackgrass 5 20 25 20 5 5 5 0 0 5 30 40 35 35 Bromegrass, Downy 5 5 1510 35 10 15 0 5 5 5 5 55 30 Canarygrass 35 40 40 10 10 0 20 0 0 0 0 0 4535 Chickweed 70 75 80 75 90 85 98 80 10 85 95 90 65 100 Cocklebur 45 8065 95 98 98 95 98 15 65 25 75 80 55 Corn 15 70 30 25 50 35 60 10 5 45 515 45 25 Crabgrass, Large 75 80 80 85 85 80 85 75 65 75 75 75 85 75Cupgrass, Woolly 70 45 75 75 90 85 85 60 50 65 65 70 98 45 Deadnettle —— — — — — — — — — — — — — Foxtail, Giant 75 75 80 85 95 85 90 75 75 7585 80 85 80 Foxtail, Green 85 60 80 85 95 90 90 90 60 75 55 65 75 50Galium — — — — — — — — — — — — — — Goosegrass 65 65 70 75 95 85 85 65 6575 90 70 85 80 Johnsongrass 65 65 65 70 70 45 60 25 15 15 45 40 90 40Kochia 0 65 25 98 85 95 85 60 10 65 45 75 65 100 Lambsquarters 65 95 8585 98 95 100 95 60 80 98 95 95 100 Morningglory 75 98 85 80 80 90 95 7060 60 15 50 75 85 Nutsedge, Yellow 70 75 75 70 35 35 20 25 45 10 10 6075 45 Oat, Wild 30 5 10 10 50 5 30 0 5 10 20 10 45 40 Pigweed 90 98 9595 98 95 98 95 70 75 98 95 98 100 Ragweed 60 85 75 85 85 95 90 85 45 7580 75 80 70 Ryegrass, Italian 10 5 5 5 0 0 0 0 0 0 5 5 30 30 Soybean 7575 75 98 98 98 98 95 60 70 85 60 70 95 Surinam Grass 75 75 80 75 80 8580 60 50 65 65 65 85 55 Velvetleaf 90 90 90 95 95 95 95 85 65 95 85 8095 100 Wheat 30 15 15 10 0 0 5 0 5 5 0 5 50 30 Windgrass 30 60 10 50 6560 65 0 5 35 50 50 70 55 Compounds 62 g ai/ha 156 157 159 160 162 164169 173 181 184 186 187 189 190 Postemergence Barley 45 15 50 30 35 5 020 40 40 5 5 5 5 Bermudagrass 90 90 100 75 95 98 75 98 100 100 80 85 15100 Blackgrass 5 5 25 10 40 5 5 10 5 35 0 0 0 30 Bromegrass, Downy 10 4050 5 30 80 40 25 50 50 25 30 5 30 Canarygrass 30 70 90 20 50 85 80 35 8050 25 35 0 5 Chickweed 98 100 100 95 100 90 100 95 100 100 98 100 100100 Cocklebur 40 100 100 100 100 100 100 65 100 100 100 100 70 90 Corn10 80 75 40 75 25 55 25 85 80 10 65 20 0 Crabgrass, Large 55 95 95 90 9098 95 80 100 100 85 98 75 65 Cupgrass, Woolly 50 85 85 65 100 85 98 9585 100 75 85 70 80 Deadnettle — — — — — — — — — 100 98 95 98 98 Foxtail,Giant 80 98 95 75 95 98 98 98 98 100 80 98 75 85 Foxtail, Green 60 85 9855 98 98 85 70 85 60 80 95 80 40 Galium — — — — — — — — — 50 40 50 60 50Goosegrass 70 95 90 85 70 98 95 90 98 100 95 98 80 75 Johnsongrass 45100 60 55 98 85 65 80 100 100 70 100 55 65 Kochia 10 0 45 100 45 100 10065 95 0 85 50 90 10 Lambsquarters 85 98 100 98 95 98 100 98 100 100 98100 98 98 Morningglory 80 95 65 98 80 95 95 80 100 95 100 95 100 40Nutsedge, Yellow 60 40 60 75 60 45 20 45 65 40 65 55 40 45 Oat, Wild 3550 80 30 40 40 30 50 75 80 5 30 10 0 Pigweed 95 75 98 100 100 98 100 90100 70 100 100 100 75 Ragweed 65 100 90 95 95 98 100 70 100 — 90 98 70 —Ryegrass, Italian 5 20 40 5 45 5 0 10 40 40 0 0 0 0 Soybean 90 98 95 98100 95 95 95 100 100 95 100 98 80 Surinam Grass 60 90 75 55 70 95 — — 8090 — 85 70 60 Velvetleaf 80 100 100 100 85 70 100 100 100 98 70 95 90100 Wheat 30 10 55 30 30 15 0 35 45 45 0 0 0 5 Windgrass 50 65 60 30 4540 30 65 50 80 30 50 40 50 Compounds 62 g ai/ha 191 193 197 217 218 219220 225 226 227 228 229 233 235 Postemergence Barley 50 0 5 5 30 25 1035 30 5 5 0 0 30 Bermudagrass 100 100 100 85 80 98 95 85 80 75 85 80 9598 Blackgrass 45 15 10 5 0 55 20 5 30 0 35 0 30 60 Bromegrass, Downy 4030 15 15 15 50 10 70 0 0 5 15 40 30 Canarygrass 50 5 30 20 0 55 10 85 300 0 15 5 30 Chickweed 98 98 100 95 100 100 95 40 75 75 100 85 95 100Cocklebur 98 95 100 98 — — — 100 98 80 98 90 100 — Corn 75 15 35 10 1060 50 50 80 75 85 80 50 100 Crabgrass, Large 100 90 85 85 45 95 75 85 8580 98 90 90 98 Cupgrass, Woolly 90 85 85 45 45 85 60 75 80 75 95 75 85100 Deadnettle 100 100 100 — — — — — — — — — — — Foxtail, Giant 100 8595 75 55 70 50 80 90 80 85 80 95 100 Foxtail, Green 55 50 30 60 85 80 6598 80 90 90 80 90 90 Galium 40 — 75 — — — — — — — — — — — Goosegrass 9895 98 80 10 95 85 90 80 75 80 70 95 98 Johnsongrass 100 65 85 60 — 60 6575 85 60 75 100 5 80 Kochia 10 80 80 98 85 98 65 10 85 75 100 70 85 100Lambsquarters 80 98 100 100 98 100 100 85 90 98 98 95 98 100Morningglory 65 60 100 75 70 85 65 95 98 100 100 100 80 98 Nutsedge,Yellow 40 65 55 60 15 55 25 25 65 45 45 20 5 45 Oat, Wild 60 50 40 40 4570 20 50 30 0 5 5 35 50 Pigweed 85 95 90 100 100 100 100 95 85 90 100 9598 100 Ragweed — — — 80 95 98 95 80 85 70 80 80 85 100 Ryegrass, Italian40 40 0 30 40 25 5 35 0 0 0 0 45 30 Soybean 95 98 100 85 100 98 85 95 9865 98 98 98 100 Surinam Grass 85 65 55 80 80 25 60 75 75 70 85 70 85 90Velvetleaf 80 100 80 98 100 90 90 90 85 80 100 75 85 100 Wheat 40 35 045 0 50 0 40 15 0 5 0 30 80 Windgrass 85 70 50 50 20 40 40 55 50 30 5040 55 95 Compounds 62 g ai/ha 236 237 238 239 240 243 244 245 255Postemergence Barley 0 15 30 0 5 90 65 85 35 Bermudagrass 98 98 98 100100 98 100 100 95 Blackgrass 5 70 60 5 50 80 60 70 5 Bromegrass, Downy 545 40 5 20 70 50 95 60 Canarygrass 0 40 25 0 5 98 95 95 50 Chickweed 10098 90 98 98 100 95 85 98 Cocklebur 100 — — 100 — — — — — Corn 60 98 8045 95 95 90 100 75 Crabgrass, Large 90 98 98 90 98 100 100 100 85Cupgrass, Woolly 85 100 100 95 100 95 100 100 95 Deadnettle — — — — — —— — — Foxtail, Giant 80 98 100 85 100 95 95 100 98 Foxtail, Green 95 9095 85 90 98 98 98 90 Galium — — — — — — — — — Goosegrass 90 98 98 98 9895 95 98 90 Johnsongrass 15 100 — 20 100 100 95 100 85 Kochia 98 80 9898 98 95 90 100 15 Lambsquarters 100 100 100 98 100 100 100 100 95Morningglory 95 95 — — — 100 95 100 85 Nutsedge, Yellow 15 35 20 30 1565 50 45 15 Oat, Wild 0 55 35 5 40 85 70 85 80 Pigweed 85 98 100 98 100100 100 98 98 Ragweed 95 98 100 98 98 95 98 98 90 Ryegrass, Italian 0 5025 0 15 85 60 50 30 Soybean 98 100 100 95 95 98 100 98 95 Surinam Grass70 98 100 35 98 95 95 100 80 Velvetleaf 100 90 90 100 85 100 100 100 98Wheat 10 70 45 0 35 95 80 95 40 Windgrass 50 90 70 30 80 90 70 70 80Compounds 31 g ai/ha 1 2 3 4 7 8 9 10 11 12 14 24 26 27 PostemergenceBarley 0 10 0 0 0 0 0 0 0 0 0 0 0 0 Bermudagrass 40 80 15 15 35 60 90 7080 65 70 85 40 70 Blackgrass 0 10 0 10 0 5 0 0 5 10 0 5 0 0 Bromegrass,Downy 0 35 0 10 0 5 5 0 20 5 10 25 10 5 Canarygrass 0 40 0 10 0 20 5 050 0 10 40 20 10 Chickweed 55 75 90 100 60 98 20 90 80 100 — 80 40 40Cocklebur 65 80 65 100 45 100 0 70 90 70 80 90 80 90 Corn 0 15 0 10 0 1515 15 70 25 10 30 35 35 Crabgrass, Large 40 80 60 70 30 70 70 65 80 6550 70 40 50 Cupgrass, Woolly 0 75 0 75 0 75 70 60 55 55 50 80 40 60Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 0 85 15 80 20 9875 70 75 75 50 70 60 65 Foxtail, Green 5 75 5 40 5 40 35 10 60 40 45 4035 80 Galium — — — — — — — — — — — — — — Goosegrass 60 80 15 25 20 80 6045 65 70 80 85 60 90 Johnsongrass 0 85 0 45 0 80 60 0 65 55 45 60 35 40Kochia 15 60 65 80 0 85 10 10 25 20 — 70 — — Lambsquarters 70 90 85 98 095 75 80 50 80 85 90 80 90 Morningglory 0 70 15 60 15 75 45 0 15 15 7050 50 50 Nutsedge, Yellow 15 45 15 55 0 65 20 15 25 15 20 20 30 30 Oat,Wild 5 30 0 30 0 10 0 0 50 0 30 40 40 45 Pigweed 65 85 75 100 75 98 8085 65 95 80 70 50 98 Ragweed 60 70 80 100 50 90 70 75 100 100 80 70 7085 Ryegrass, Italian 0 0 0 10 0 20 0 0 10 0 0 0 0 0 Soybean 50 80 65 9560 98 70 95 100 98 80 85 95 95 Surinam Grass 0 70 15 60 0 60 55 60 60 2540 50 30 50 Velvetleaf 55 85 95 70 70 75 85 70 80 80 85 75 70 50 Wheat 05 0 5 0 25 0 0 30 0 0 5 0 0 Windgrass 0 10 0 50 5 5 50 5 40 10 5 20 1010 Compounds 31 g ai/ha 29 33 34 36 37 38 39 40 42 44 45 46 47 48Postemergence Barley 0 0 0 5 0 0 0 0 0 0 5 0 5 5 Bermudagrass 85 75 7590 85 98 50 — 70 80 80 80 85 85 Blackgrass 10 10 0 5 0 5 0 0 5 0 5 0 5 0Bromegrass, Downy 5 5 40 30 0 50 0 45 0 40 10 0 35 10 Canarygrass 10 0 540 0 10 0 20 0 20 10 0 20 30 Chickweed 50 80 50 85 80 85 98 100 60 90 7580 85 85 Cocklebur 85 85 0 — — — 75 — 0 80 10 75 95 95 Corn 20 0 0 50 055 25 80 0 75 10 20 65 65 Crabgrass, Large 45 75 80 90 70 90 75 85 70 8565 60 85 85 Cupgrass, Woolly 80 65 80 85 55 80 65 90 15 80 70 10 85 80Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 80 75 85 95 70 9575 100 45 95 75 70 90 85 Foxtail, Green 60 50 70 85 60 85 80 90 50 90 5045 80 85 Galium — — — — — — — — — — — — — — Goosegrass 80 70 75 85 80 8040 85 70 85 75 75 90 85 Johnsongrass 20 15 75 65 0 70 65 — 0 70 60 40 8545 Kochia — 10 85 0 0 65 20 0 80 75 0 0 95 98 Lambsquarters 85 95 95 9895 90 95 100 90 90 95 80 98 85 Morningglory 60 60 60 60 60 65 65 70 4560 75 30 75 70 Nutsedge, Yellow 40 40 5 10 10 0 0 20 55 40 10 65 65 40Oat, Wild 40 10 40 60 0 55 10 85 5 50 35 0 40 40 Pigweed 60 90 70 85 8095 98 90 85 75 85 75 98 85 Ragweed 80 90 75 90 80 75 85 98 70 85 80 7085 85 Ryegrass, Italian 5 5 10 0 0 35 0 0 0 5 30 0 0 0 Soybean 85 95 8590 75 85 95 100 70 95 80 75 95 95 Surinam Grass 50 45 70 75 60 70 60 8540 85 70 45 85 70 Velvetleaf 50 80 80 98 75 95 75 98 80 95 70 75 80 85Wheat 0 0 0 5 0 0 5 0 0 5 10 0 0 0 Windgrass 5 10 10 50 5 70 0 70 10 6530 10 60 70 Compounds 31 g ai/ha 49 50 51 52 53 55 56 58 59 61 62 63 6466 Postemergence Barley 0 0 5 0 0 0 0 5 0 0 0 0 15 0 Bermudagrass 75 9080 85 90 80 75 85 — 75 — — 95 70 Blackgrass 0 5 0 5 20 0 0 5 10 0 15 300 5 Bromegrass, Downy 0 0 50 50 35 0 35 40 5 0 30 10 25 5 Canarygrass 00 60 0 40 0 0 60 5 0 0 0 40 0 Chickweed 75 80 80 95 85 65 90 70 85 80 7060 98 80 Cocklebur 65 85 85 75 80 45 5 85 85 0 25 65 90 10 Corn 5 5 7530 55 0 45 0 — 0 70 — 80 25 Crabgrass, Large 75 75 80 85 85 60 75 75 8065 55 70 85 50 Cupgrass, Woolly 50 70 75 70 65 10 15 65 75 55 55 50 7540 Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 45 75 80 80 8025 75 75 75 55 55 60 90 65 Foxtail, Green 50 80 85 95 95 30 80 75 50 5040 60 70 80 Galium — — — — — — — — — — — — — — Goosegrass 65 75 75 75 7545 65 70 75 40 65 70 80 65 Johnsongrass 0 0 75 75 55 0 55 50 — 0 0 — 9045 Kochia 55 95 20 20 45 20 90 0 — 5 10 10 50 80 Lambsquarters 70 98 7585 90 80 98 95 95 85 85 — 95 95 Morningglory 65 10 75 10 55 55 — 65 — 45— — 80 98 Nutsedge, Yellow 65 70 60 20 20 10 20 25 45 20 15 20 0 25 Oat,Wild 0 5 60 90 50 0 5 45 30 0 5 0 60 0 Pigweed 80 80 85 85 85 80 98 80 —80 98 85 98 98 Ragweed 75 80 80 75 80 70 55 80 75 75 70 70 85 0Ryegrass, Italian 0 0 0 40 0 0 0 0 5 0 0 0 0 0 Soybean 55 85 85 80 90 2585 85 90 0 75 75 85 95 Surinam Grass 15 65 80 75 85 10 75 70 75 20 20 1085 65 Velvetleaf 90 90 80 95 85 90 85 75 85 80 85 95 85 85 Wheat 0 0 515 20 0 0 0 0 0 0 0 10 0 Windgrass 0 10 50 60 60 0 30 35 20 0 30 10 7060 Compounds 31 g ai/ha 67 68 69 70 71 72 73 74 75 77 79 80 81 82Postemergence Barley 0 0 5 10 0 0 0 0 0 0 5 15 0 0 Bermudagrass 35 75 9875 65 75 65 75 90 90 80 20 85 80 Blackgrass 0 0 0 30 0 0 0 0 0 0 5 0 5 0Bromegrass, Downy 0 5 40 10 0 0 20 0 5 0 5 45 5 0 Canarygrass 0 0 0 50 00 0 0 0 0 15 45 0 0 Chickweed 90 85 98 80 75 70 80 75 85 80 80 90 95 90Cocklebur 75 25 0 0 65 75 0 20 40 0 95 0 5 85 Corn 5 0 5 15 0 0 20 0 0 05 5 5 0 Crabgrass, Large 75 75 95 80 65 75 80 80 95 55 80 75 85 70Cupgrass, Woolly 60 10 90 45 10 45 60 10 10 20 10 65 65 55 Deadnettle —— — — — — — — — — — — — — Foxtail, Giant 75 65 95 75 20 65 70 25 75 6570 75 75 75 Foxtail, Green 10 40 95 80 60 10 70 20 65 40 60 90 5 60Galium — — — — — — — — — — — — — — Goosegrass 55 65 75 75 75 60 65 65 7565 45 70 65 75 Johnsongrass 0 10 98 65 65 0 10 0 0 0 0 0 5 65 Kochia 7570 60 65 0 75 75 75 75 75 75 0 75 10 Lambsquarters 80 95 100 85 75 90 8595 98 95 95 95 95 80 Morningglory 80 80 70 98 65 20 0 60 20 75 80 85 7565 Nutsedge, Yellow 60 0 5 10 10 35 20 20 10 45 25 10 65 10 Oat, Wild 05 60 55 0 0 55 20 0 0 40 20 25 0 Pigweed 98 85 98 85 85 80 80 90 100 98100 100 98 75 Ragweed 75 75 90 60 75 75 75 75 80 75 80 50 75 75Ryegrass, Italian 0 5 30 10 0 0 35 5 0 0 20 0 0 0 Soybean 80 80 80 75 6580 80 75 80 25 75 75 85 75 Surinam Grass 10 25 85 65 50 75 80 20 50 6520 45 75 65 Velvetleaf 90 95 95 75 75 98 95 98 100 90 95 85 100 85 Wheat5 5 5 5 0 0 0 5 0 0 10 5 5 0 Windgrass 0 40 60 80 5 5 70 5 30 10 50 5010 5 Compounds 31 g ai/ha 83 85 86 87 88 89 90 91 92 93 94 95 96 97Postemergence Barley 0 5 30 0 30 0 0 0 0 0 0 0 0 0 Bermudagrass 75 85 8590 80 75 70 75 20 60 80 45 80 95 Blackgrass 0 5 15 5 0 10 5 10 0 0 5 0 55 Bromegrass, Downy 40 0 10 20 40 0 5 0 0 0 0 0 0 0 Canarygrass 20 35 200 60 10 5 25 0 0 0 0 0 0 Chickweed 90 85 80 100 75 75 70 85 90 80 95 7575 95 Cocklebur 75 95 85 98 90 10 75 20 25 70 45 70 75 95 Corn 0 50 1020 15 80 15 25 20 0 0 0 45 20 Crabgrass, Large 85 90 85 85 95 85 65 8080 70 70 45 75 75 Cupgrass, Woolly 70 75 75 50 75 35 45 70 10 45 — 45 7055 Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 80 75 90 75 9570 65 85 65 70 65 45 65 60 Foxtail, Green 90 80 70 75 95 60 65 70 75 5010 20 50 40 Galium — — — — — — — — — — — — — — Goosegrass 75 70 70 75 6555 60 30 60 60 45 65 70 60 Johnsongrass 95 80 95 5 95 25 10 65 20 10 — 520 15 Kochia 65 75 75 100 75 65 65 20 75 65 — 80 65 65 Lambsquarters 9598 100 98 95 95 85 85 90 85 80 80 90 90 Morningglory 70 95 70 45 90 7065 75 80 70 55 100 65 100 Nutsedge, Yellow 10 75 65 10 25 35 60 50 45 4520 75 70 75 Oat, Wild 10 5 20 50 50 10 0 30 0 0 0 0 0 0 Pigweed 80 10098 98 98 80 85 100 90 90 100 85 90 95 Ragweed 75 80 80 85 75 70 60 85 4065 40 75 80 85 Ryegrass, Italian 0 0 25 5 5 0 0 0 0 0 0 0 0 0 Soybean 7580 80 98 75 90 98 75 90 55 65 95 65 70 Surinam Grass 75 75 80 75 95 5565 85 25 50 — 45 75 65 Velvetleaf 85 90 98 100 80 90 85 98 95 85 — 85 95100 Wheat 0 0 5 35 0 0 5 0 0 0 0 0 0 0 Windgrass 5 40 30 55 40 0 0 10 05 0 0 5 5 Compounds 31 g ai/ha 98 99 100 102 107 108 109 111 113 117 118119 120 121 Postemergence Barley 0 5 5 0 0 0 0 0 0 0 0 0 — 0Bermudagrass 75 75 70 80 75 85 70 95 80 75 75 75 80 95 Blackgrass 0 0 00 0 0 0 5 0 0 5 5 30 5 Bromegrass, Downy 5 5 5 0 0 0 0 0 5 5 0 10 20 25Canarygrass 5 40 0 5 5 0 0 0 65 0 0 5 0 0 Chickweed 80 80 75 60 98 85 9095 98 85 90 70 60 100 Cocklebur 98 95 40 90 98 75 75 98 95 75 40 0 10 40Corn 35 40 0 — 65 15 0 10 25 10 0 20 15 25 Crabgrass, Large 75 85 55 7075 60 65 70 85 75 70 75 80 85 Cupgrass, Woolly 65 70 — 70 65 40 — 40 8565 65 75 70 95 Deadnettle — — — — — — — — — — — — — — Foxtail, Giant 6575 70 70 75 45 70 60 80 65 75 75 75 95 Foxtail, Green 30 50 20 80 70 520 40 80 50 50 85 90 80 Galium — — — — — — — — — — — — — — Goosegrass 6075 70 55 75 60 65 70 70 45 55 75 75 95 Johnsongrass 55 70 0 20 60 10 510 65 5 10 10 15 20 Kochia 65 80 — 65 98 70 70 80 98 45 45 40 10 95Lambsquarters 95 98 95 95 90 98 98 98 95 95 85 85 80 95 Morningglory 70100 60 65 100 75 70 100 98 10 10 10 15 5 Nutsedge, Yellow 50 45 — 45 7550 — 65 65 0 35 10 5 5 Oat, Wild 10 10 0 5 0 0 0 0 20 5 5 50 50 60Pigweed 100 100 90 70 95 95 100 95 95 95 85 95 95 100 Ragweed 70 65 7070 75 80 75 75 80 70 70 70 50 65 Ryegrass, Italian 0 0 5 0 0 0 0 0 40 05 5 10 40 Soybean 90 98 95 75 95 45 95 70 98 65 75 0 40 90 Surinam Grass65 70 — 60 75 55 65 60 85 65 50 75 20 95 Velvetleaf 95 95 — 98 90 100 9080 85 70 75 75 75 98 Wheat 0 0 0 0 0 0 0 0 0 0 0 10 20 5 Windgrass 0 5 05 5 0 30 0 5 40 50 60 60 80 Compounds 31 g ai/ha 122 123 126 127 128 129130 131 140 141 146 147 152 155 Postemergence Barley 0 5 5 0 0 0 0 0 0 00 0 10 30 Bermudagrass 75 80 75 95 75 80 75 65 60 80 85 75 95 85Blackgrass 5 20 5 5 5 0 0 0 0 5 5 10 20 10 Bromegrass, Downy 5 0 5 5 305 10 0 0 0 0 0 30 5 Canarygrass 10 25 15 5 10 0 5 0 0 0 0 0 35 10Chickweed 70 70 65 65 90 85 98 65 0 60 70 70 10 100 Cocklebur 20 65 1575 98 95 85 95 0 40 10 50 70 15 Corn 0 35 10 5 40 20 55 0 0 0 0 0 25 5Crabgrass, Large 75 70 75 80 85 80 85 75 50 70 65 60 75 60 Cupgrass,Woolly 65 25 65 75 85 80 80 50 50 65 60 65 95 20 Deadnettle — — — — — —— — — — — — — — Foxtail, Giant 70 65 70 80 95 70 90 75 65 75 75 65 80 65Foxtail, Green 80 50 50 75 85 80 90 70 45 50 50 40 75 25 Galium — — — —— — — — — — — — — — Goosegrass 40 65 65 65 90 85 85 65 45 65 75 35 80 65Johnsongrass 45 35 65 65 70 40 60 5 10 15 45 15 70 10 Kochia 0 60 10 4560 80 85 35 0 20 40 40 10 35 Lambsquarters 60 80 70 75 95 90 98 85 45 8095 85 85 98 Morningglory 60 70 75 65 80 90 95 70 0 60 0 50 45 55Nutsedge, Yellow 55 65 65 65 20 35 10 15 10 0 5 50 65 20 Oat, Wild 5 0 55 40 0 20 0 0 10 0 5 30 10 Pigweed 85 80 75 80 95 85 95 90 55 60 95 8595 98 Ragweed 60 70 55 70 85 90 85 80 25 65 65 20 60 45 Ryegrass,Italian 5 0 0 0 0 0 0 0 0 0 5 5 5 5 Soybean 45 60 70 95 98 95 98 75 1070 70 15 70 95 Surinam Grass 75 25 70 75 50 80 80 20 50 40 65 50 75 40Velvetleaf 80 80 80 90 90 95 95 80 50 75 80 60 85 100 Wheat 15 10 5 5 00 5 0 5 0 0 0 35 15 Windgrass 5 30 10 25 50 45 60 0 0 25 45 10 50 50Compounds 31 g ai/ha 156 157 159 160 162 164 169 173 181 184 186 187 189190 Postemergence Barley 30 5 20 5 30 5 0 5 5 5 0 0 0 0 Bermudagrass 8075 95 65 85 70 70 98 100 98 80 75 10 98 Blackgrass 5 0 20 5 30 5 5 5 030 0 0 0 5 Bromegrass, Downy 10 40 50 0 20 40 10 5 40 40 5 5 0 5Canarygrass 15 40 80 5 40 40 40 10 50 45 5 10 0 0 Chickweed 80 100 10085 90 80 100 65 100 100 95 100 98 — Cocklebur 20 100 95 98 100 98 100 60100 100 90 100 60 40 Corn 10 70 60 15 50 15 45 5 70 80 10 50 20 0Crabgrass, Large 45 80 80 80 80 95 85 70 98 100 80 85 75 60 Cupgrass,Woolly 40 85 70 65 90 75 85 85 80 75 70 80 70 75 Deadnettle — — — — — —— — — 100 90 80 85 65 Foxtail, Giant 75 98 85 70 85 90 95 95 98 98 75 9875 70 Foxtail, Green 45 70 85 55 98 70 60 55 70 30 50 65 65 25 Galium —— — — — — — — — 50 40 20 20 50 Goosegrass 65 85 85 80 60 85 95 80 95 10085 85 60 70 Johnsongrass 15 70 45 45 98 45 60 65 100 100 65 90 50 60Kochia 10 0 40 90 20 98 100 65 65 0 75 40 85 0 Lambsquarters 80 98 10095 80 98 100 98 100 80 98 98 98 80 Morningglory 80 20 60 75 75 90 95 7595 40 95 80 100 40 Nutsedge, Yellow 45 30 40 65 25 40 0 45 60 35 65 4520 35 Oat, Wild 5 30 60 10 35 25 0 50 65 40 0 10 5 0 Pigweed 60 65 95 90100 98 100 85 100 70 85 100 80 65 Ragweed 65 90 90 80 90 85 100 55 98 —85 95 10 — Ryegrass, Italian 0 10 30 0 40 5 0 0 10 20 0 0 0 0 Soybean 8095 95 85 98 80 90 60 100 98 85 98 90 80 Surinam Grass 40 75 75 40 65 60— — 70 80 — 65 65 60 Velvetleaf 60 100 100 90 80 70 100 100 100 85 70 9085 100 Wheat 15 0 40 10 10 0 0 10 40 30 0 0 0 0 Windgrass 40 60 45 20 405 15 30 40 60 10 10 25 15 Compounds 31 g ai/ha 191 193 197 217 218 219220 225 226 227 228 229 233 235 Postemergence Barley 5 0 0 0 30 0 10 2010 0 0 0 0 0 Bermudagrass 100 95 95 70 70 95 80 80 80 75 80 75 95 98Blackgrass 30 10 0 0 0 50 10 0 5 0 5 0 5 45 Bromegrass, Downy 35 10 1510 5 45 10 35 0 0 5 5 40 10 Canarygrass 20 5 5 0 0 35 10 60 5 0 0 5 0 20Chickweed 98 95 100 75 100 100 95 25 75 65 98 70 90 98 Cocklebur 90 9580 80 — — — 98 98 75 98 85 90 — Corn 65 0 15 0 0 10 25 40 75 20 80 70 3095 Crabgrass, Large 85 75 75 80 40 90 70 75 85 80 80 80 80 98 Cupgrass,Woolly 85 75 70 25 40 85 60 75 80 55 75 70 80 95 Deadnettle 90 100 100 —— — — — — — — — — — Foxtail, Giant 100 75 85 70 40 70 30 75 85 75 85 7590 98 Foxtail, Green 40 40 5 55 60 70 60 85 70 50 85 40 85 90 Galium 2075 75 — — — — — — — — — — — Goosegrass 95 85 85 80 0 90 80 85 80 75 8070 85 95 Johnsongrass 70 50 70 0 — — 60 60 85 45 75 70 0 70 Kochia 5 2065 75 35 80 45 5 80 70 90 55 70 98 Lambsquarters 75 98 95 90 98 100 10085 90 90 98 85 98 98 Morningglory 40 40 98 70 70 60 65 95 98 100 100 9865 95 Nutsedge, Yellow 40 60 45 10 10 10 10 10 55 10 40 0 0 45 Oat, Wild50 0 40 30 40 50 10 45 25 0 0 0 30 35 Pigweed 80 90 80 85 100 100 95 9075 80 98 80 85 100 Ragweed — — — 80 95 80 90 75 80 60 70 80 80 98Ryegrass, Italian 40 5 0 0 30 20 5 0 0 0 0 0 30 30 Soybean 90 80 98 7585 95 80 85 95 55 95 95 98 98 Surinam Grass 70 65 50 70 75 10 50 75 7555 75 65 80 80 Velvetleaf 75 90 80 98 85 85 80 80 85 80 80 75 80 95Wheat 35 30 0 30 0 40 0 30 10 0 0 0 10 45 Windgrass 55 50 10 50 10 35 550 10 0 5 0 50 85 Compounds 31 g ai/ha 236 237 238 239 240 243 244 245255 Postemergence Barley 0 5 10 0 5 60 50 45 30 Bermudagrass 95 98 95 9598 98 80 80 90 Blackgrass 0 50 40 5 40 60 50 40 5 Bromegrass, Downy 0 3010 0 10 50 40 60 50 Canarygrass 0 30 20 0 5 90 80 80 50 Chickweed 75 9080 90 90 80 80 80 95 Cocklebur — — — 90 — — — — — Corn 15 85 80 5 90 9085 100 60 Crabgrass, Large 75 95 95 75 80 95 80 80 85 Cupgrass, Woolly70 100 95 75 98 95 100 100 85 Deadnettle — — — — — — — — — Foxtail,Giant 75 98 100 75 100 95 95 98 95 Foxtail, Green 80 80 85 80 90 98 8585 85 Galium — — — — — — — — — Goosegrass 80 95 95 80 95 95 85 98 90Johnsongrass 0 100 60 0 — 100 85 100 80 Kochia 80 65 90 90 80 85 85 8510 Lambsquarters 98 95 100 98 98 100 100 98 90 Morningglory 60 85 — 95 —95 90 90 75 Nutsedge, Yellow 0 20 20 30 10 65 45 40 10 Oat, Wild 0 40 300 25 80 50 70 65 Pigweed 85 80 100 95 — 85 95 80 80 Ragweed 80 95 100 9598 90 98 95 50 Ryegrass, Italian 0 50 20 0 10 60 35 40 10 Soybean 90 9598 70 95 95 85 95 95 Surinam Grass 60 85 95 25 95 90 90 100 80Velvetleaf 98 85 80 100 75 100 100 100 95 Wheat 0 50 40 0 30 85 60 75 35Windgrass 30 60 45 20 60 80 50 65 50 Compounds 16 g ai/ha 2 69 122 131159 169 225 Postemergence Barley 0 0 0 0 20 0 5 Bermudagrass 40 85 65 6080 70 40 Blackgrass 0 0 0 0 5 0 0 Bromegrass, Downy 20 30 5 0 15 0 30Canarygrass 20 0 0 0 40 5 55 Chickweed 70 95 65 45 100 90 15 Cocklebur75 0 0 80 80 100 85 Corn 15 0 0 0 25 20 10 Crabgrass, Large 70 95 65 6575 75 70 Cupgrass, Woolly 75 75 65 10 65 75 70 Foxtail, Giant 70 80 6565 80 75 75 Foxtail, Green 50 75 40 40 80 45 85 Goosegrass 80 75 10 6580 80 80 Johnsongrass 75 75 20 0 45 40 20 Kochia 55 60 0 20 20 100 5Lambsquarters 80 100 55 75 95 95 85 Morningglory 55 65 55 5 10 95 80Nutsedge, Yellow 40 5 35 0 20 0 5 Oat, Wild 5 50 5 0 35 0 25 Pigweed 7095 75 60 75 90 80 Ragweed 65 75 55 65 80 98 70 Ryegrass, Italian 0 0 5 00 0 0 Soybean 75 45 20 75 85 55 65 Surinam Grass 70 75 25 15 65 — 35Velvetleaf — 75 75 70 100 75 80 Wheat 0 0 5 0 35 0 20 Windgrass 10 40 50 40 5 5 Compound 8 g ai/ha 159 Postemergence Barley 0 Bermudagrass 70Blackgrass 0 Bromegrass, Downy 15 Canarygrass 25 Chickweed 80 Cocklebur75 Corn 15 Crabgrass, Large 65 Cupgrass, Woolly 60 Foxtail, Giant 75Foxtail, Green 50 Goosegrass 70 Johnsongrass 10 Kochia 20 Lambsquarters90 Morningglory 0 Nutsedge, Yellow 10 Oat, Wild 0 Pigweed 55 Ragweed 65Ryegrass, Italian 0 Soybean 80 Surinam Grass 65 Velvetleaf 98 Wheat 10Windgrass 10 Compounds 250 g ai/ha 3 7 9 10 11 12 14 24 26 27 29 33 3436 Preemergence Bermudagrass 90 98 100 100 100 100 100 100 100 100 100100 100 100 Blackgrass 0 0 40 20 60 10 0 10 10 30 50 30 50 25Bromegrass, Downy 0 0 10 0 5 0 0 20 10 30 5 30 80 10 Cocklebur 100 75100 98 100 100 95 95 98 90 90 90 85 80 Corn 5 0 10 0 35 75 10 5 0 0 0 00 0 Crabgrass, Large 100 95 100 95 100 100 100 100 100 100 100 100 100100 Cupgrass, Woolly 10 45 60 40 75 85 70 90 85 80 90 85 100 65 Foxtail,Giant 0 25 98 45 100 100 90 100 90 95 100 98 100 80 Foxtail, Green 0 0 —30 65 80 60 100 70 80 100 100 100 85 Galium 50 0 95 85 75 95 80 80 98 95100 90 98 95 Goosegrass 98 60 100 98 100 100 100 100 100 100 100 98 100100 Johnsongrass 10 0 98 75 98 98 95 90 90 85 90 20 100 85 Kochia 100100 100 100 100 100 100 100 100 100 100 — — — Lambsquarters 100 100 100100 100 100 100 100 100 100 100 100 100 100 Morningglory 100 20 98 40100 100 100 100 100 100 100 90 98 20 Nightshade 100 100 100 100 100 100100 100 100 100 100 100 100 98 Nutsedge, Yellow 50 55 95 75 90 90 85 9085 90 85 90 90 75 Oat, Wild 0 0 60 10 40 5 0 80 5 50 50 50 60 0 Pigweed95 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 90 90 100100 100 100 90 100 100 100 100 100 90 90 Russian Thistle — — — — — — — —— — — — — — Ryegrass, Italian 0 0 40 0 0 0 0 10 0 0 40 5 10 0 Soybean 5030 80 75 95 95 85 85 90 90 95 75 80 40 Sunflower 85 25 98 98 98 100 9898 95 100 100 90 90 85 Surinam Grass 5 10 95 80 75 100 80 100 90 95 95100 90 100 Velvetleaf 100 100 100 100 100 100 100 100 100 95 100 100 100100 Wheat 0 0 5 5 5 0 0 0 0 5 0 5 0 0 Compounds 250 g ai/ha 37 38 39 4042 44 45 46 47 48 49 50 51 52 Preemergence Bermudagrass 100 100 100 100100 100 100 98 100 100 100 100 100 100 Blackgrass 10 40 0 5 5 60 5 0 5 50 5 20 10 Bromegrass, Downy 0 40 0 10 0 5 5 0 10 45 — 0 40 5 Cocklebur45 90 45 100 — 45 — 15 — 85 55 — 75 75 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0Crabgrass, Large 100 100 100 100 100 100 100 98 100 100 100 100 100 100Cupgrass, Woolly 70 80 10 85 5 85 75 60 90 95 20 70 85 80 Foxtail, Giant75 95 75 98 10 98 75 25 100 98 45 90 75 75 Foxtail, Green 90 100 100 10085 100 100 10 98 98 30 100 100 100 Galium 100 85 85 90 50 98 85 70 95 7095 98 95 95 Goosegrass 100 100 100 100 100 100 100 98 100 100 100 100100 100 Johnsongrass 90 95 75 90 65 95 85 70 100 98 10 95 80 95 Kochia —— — — — — — — — — — — — — Lambsquarters 100 100 100 100 100 100 100 100100 100 98 100 98 100 Morningglory 0 100 100 65 0 95 0 0 55 100 85 55 7055 Nightshade 85 100 100 100 100 100 100 98 100 100 98 100 100 100Nutsedge, Yellow 90 80 10 85 85 90 70 90 90 90 90 90 90 90 Oat, Wild 1020 0 30 0 30 5 0 10 15 0 0 0 60 Pigweed 100 100 100 100 100 100 100 100100 100 100 100 100 100 Ragweed 98 95 95 95 80 95 95 100 95 95 95 100 9095 Russian Thistle — — — — — — — — — — — — — — Ryegrass, Italian 0 40 05 0 0 0 0 0 0 5 0 5 0 Soybean 35 75 0 70 0 0 0 25 0 20 85 0 85 80Sunflower 90 75 65 80 75 80 75 60 85 80 75 85 75 75 Surinam Grass 100 8015 90 75 100 98 90 100 100 85 100 100 98 Velvetleaf 98 100 98 100 90 10095 65 100 100 100 100 100 100 Wheat 0 5 0 — 0 0 0 0 0 0 0 0 10 0Compounds 250 g ai/ha 53 55 56 58 59 61 62 63 64 66 67 68 72 73Preemergence Bermudagrass 100 100 100 100 98 98 100 98 98 98 100 100 100100 Blackgrass 60 30 5 30 40 0 0 40 0 5 5 5 5 10 Bromegrass, Downy 30 05 0 0 0 0 0 0 0 0 5 0 20 Cocklebur 70 15 0 65 75 65 10 10 70 0 20 80 8065 Corn 20 0 0 0 0 0 — 0 0 0 0 0 0 10 Crabgrass, Large 100 98 98 100 9898 98 100 98 100 100 100 100 100 Cupgrass, Woolly 95 55 70 85 85 0 10 1010 75 10 85 65 80 Foxtail, Giant 100 10 80 75 75 45 20 10 65 80 65 75 6580 Foxtail, Green 98 0 100 100 98 75 10 30 50 75 40 85 90 80 Galium 9085 85 80 98 98 0 20 70 0 90 85 85 85 Goosegrass 100 98 100 100 100 98 98100 100 98 98 98 100 100 Johnsongrass 75 0 80 85 90 20 — 60 75 98 0 9510 98 Kochia — — — — 98 — 100 100 95 85 85 95 85 90 Lambsquarters 100100 98 98 100 — 100 100 98 100 98 100 100 100 Morningglory 65 65 65 7560 65 20 55 0 80 80 85 75 70 Nightshade 100 100 100 100 100 — 98 98 9898 98 100 100 100 Nutsedge, Yellow 90 65 90 90 90 90 — 90 10 95 75 90 9085 Oat, Wild 70 0 0 30 0 0 0 0 5 40 0 5 0 65 Pigweed 100 100 100 100 100— 100 100 98 98 98 100 100 100 Ragweed 90 90 80 90 95 90 60 85 85 55 5090 85 85 Russian Thistle — — — — — — — — — — 90 98 80 — Ryegrass,Italian 50 0 0 0 20 5 20 0 0 5 0 0 0 5 Soybean 85 65 90 95 80 20 — 15 —— — — — — Sunflower 65 70 75 75 80 70 55 70 55 10 55 85 80 75 SurinamGrass 100 45 98 95 95 35 60 85 90 100 75 85 98 100 Velvetleaf 100 100 9895 100 100 95 100 100 100 100 100 100 100 Wheat 10 0 10 0 0 0 0 0 0 0 00 0 30 Compounds 250 g ai/ha 74 75 77 81 113 119 120 193 217 218 219 220243 244 Preemergence Bermudagrass 100 100 100 100 100 100 100 98 100 100100 100 100 100 Blackgrass 10 10 0 35 20 70 50 70 0 20 60 35 95 70Bromegrass, Downy 0 0 0 0 10 55 85 50 0 0 20 5 70 30 Cocklebur 80 90 6585 100 85 98 95 85 100 85 0 98 100 Corn 0 0 0 55 0 50 55 5 0 0 0 0 95 85Crabgrass, Large 100 100 100 100 100 100 100 100 100 98 100 100 100 100Cupgrass, Woolly 5 75 0 85 95 100 90 90 80 85 80 25 100 100 Foxtail,Giant 45 80 45 98 85 100 100 80 85 85 80 75 95 100 Foxtail, Green 0 9815 100 100 100 100 98 90 100 100 100 100 90 Galium 98 98 90 100 95 10098 100 90 100 100 100 100 98 Goosegrass 100 100 98 100 100 100 100 100100 98 100 100 100 100 Johnsongrass 0 70 0 90 70 95 90 60 55 45 80 80100 100 Kochia 85 95 95 70 90 98 75 90 — — — — 100 100 Lambsquarters 100100 100 98 100 100 100 100 100 100 100 100 100 100 Morningglory 80 90 9095 — 95 100 95 0 65 100 90 100 100 Nightshade 100 100 100 100 100 100 98100 100 100 100 100 98 100 Nutsedge, Yellow 90 90 90 95 90 98 98 90 9090 90 90 95 95 Oat, Wild 5 0 0 0 40 80 65 60 0 0 40 60 90 40 Pigweed 100100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 100 95 95 9098 95 95 100 95 100 98 95 98 100 Russian Thistle 98 — — 100 — 100 — 100— — — — 100 — Ryegrass, Italian 0 0 0 0 40 100 100 45 10 5 10 0 70 45Soybean — — — — 90 80 80 80 0 90 75 75 95 95 Sunflower 85 85 85 90 95 8595 95 85 95 85 90 95 100 Surinam Grass 95 75 100 100 98 100 100 45 90100 100 65 100 100 Velvetleaf 100 100 100 100 100 100 100 100 100 100 95100 100 100 Wheat 0 0 0 0 10 50 30 25 0 0 0 5 70 45 Compounds 250 gai/ha 245 255 Preemergence Bermudagrass 100 100 Blackgrass 45 60Bromegrass, Downy 15 40 Cocklebur 100 — Corn 65 0 Crabgrass, Large 100100 Cupgrass, Woolly 100 90 Foxtail, Giant 100 98 Foxtail, Green 100 100Galium 95 100 Goosegrass 100 100 Johnsongrass 100 98 Kochia 100 —Lambsquarters 100 100 Morningglory 100 90 Nightshade 100 100 Nutsedge,Yellow 80 90 Oat, Wild 30 90 Pigweed 100 100 Ragweed 100 100 RussianThistle — — Ryegrass, Italian 40 30 Soybean 75 80 Sunflower 95 90Surinam Grass 100 100 Velvetleaf 100 100 Wheat 15 5 Compounds 125 gai/ha 2 3 7 9 10 11 12 14 24 26 27 29 33 34 Preemergence Bermudagrass100 80 85 100 100 100 100 100 100 98 100 100 100 100 Blackgrass 50 0 020 0 30 5 0 0 0 10 50 10 50 Bromegrass, Downy 5 0 0 5 0 0 0 0 0 0 0 0 510 Cocklebur 80 70 0 65 65 95 98 85 95 85 85 90 85 75 Corn 0 0 0 0 0 015 0 0 0 0 0 0 0 Crabgrass, Large 100 85 45 100 70 100 100 100 100 100100 100 100 100 Cupgrass, Woolly 20 0 0 45 35 15 75 50 85 50 60 55 60100 Foxtail, Giant 70 0 0 60 0 75 70 75 90 45 85 100 95 90 Foxtail,Green 60 0 0 5 0 65 40 10 100 30 50 100 100 90 Galium — 30 0 60 85 50 9040 10 90 85 98 50 90 Goosegrass 100 85 45 100 95 100 100 98 100 95 100100 90 100 Johnsongrass 80 0 0 90 60 85 75 80 90 60 50 30 0 98 Kochia100 100 100 100 100 100 100 100 100 100 100 100 — — Lambsquarters 100100 100 100 100 100 100 100 100 100 100 100 100 100 Morningglory 75 1000 70 0 35 85 100 100 100 100 100 70 75 Nightshade 100 98 95 100 100 100100 100 100 100 100 100 100 100 Nutsedge, Yellow 70 40 15 80 55 85 75 4085 50 30 60 70 75 Oat, Wild 50 0 0 0 0 10 0 0 0 0 30 45 30 30 Pigweed100 90 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed 98 90 15100 100 100 100 90 98 95 100 100 100 90 Russian Thistle — — — — — — — —— — — — — — Ryegrass, Italian 5 0 0 0 0 0 0 0 10 0 0 10 5 5 Soybean 7035 20 — 65 65 80 50 80 80 80 90 65 65 Sunflower 90 70 0 95 95 95 98 8595 90 90 90 75 80 Surinam Grass 60 0 0 95 15 35 95 60 95 90 60 90 95 65Velvetleaf 100 90 100 100 100 100 100 100 100 100 90 100 100 95 Wheat 00 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha 36 37 38 39 40 42 44 4546 47 48 49 50 51 Preemergence Bermudagrass 100 98 100 100 100 100 100100 — 100 100 98 100 100 Blackgrass 25 5 30 0 0 0 40 0 0 5 0 0 0 10Bromegrass, Downy 0 0 5 0 5 0 0 0 0 5 0 0 0 5 Cocklebur — 0 25 — 85 — —— 0 — 0 45 75 20 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 10010 100 100 100 95 100 100 85 100 100 98 100 100 Cupgrass, Woolly 10 1060 0 70 0 80 60 50 75 75 0 15 75 Foxtail, Giant 65 0 80 70 80 10 75 4515 85 85 20 90 50 Foxtail, Green 85 0 85 75 85 85 98 80 5 98 98 5 95 98Galium 80 30 85 85 85 10 65 50 0 50 60 90 95 80 Goosegrass 95 80 100 100100 100 100 100 98 100 100 98 100 100 Johnsongrass 80 45 85 65 85 10 9075 45 80 90 0 90 75 Kochia — — — — — — — — — — — — — — Lambsquarters 100100 100 100 100 100 100 100 95 100 100 98 100 98 Morningglory 0 0 0 15 00 50 — 0 0 100 80 — 20 Nightshade 95 80 98 100 98 100 100 100 98 100 10098 100 98 Nutsedge, Yellow 40 20 70 0 65 75 75 20 80 80 85 85 90 85 Oat,Wild 0 0 0 0 0 0 5 0 0 0 0 0 0 0 Pigweed 100 100 100 100 100 100 100 10095 100 100 100 100 100 Ragweed 85 65 80 75 90 25 95 80 100 90 90 80 9580 Russian Thistle — — — — — — — — — — — — — — Ryegrass, Italian 0 0 5 05 0 0 0 0 0 0 0 0 0 Soybean 0 0 0 0 20 0 0 0 15 0 0 85 — 80 Sunflower 5545 25 25 75 55 75 10 0 80 80 75 85 75 Surinam Grass 100 55 65 10 85 1090 98 75 100 100 75 98 98 Velvetleaf 100 20 98 75 100 85 100 85 55 90100 100 100 98 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 125 g ai/ha52 53 55 56 58 59 61 62 63 64 66 67 68 69 Preemergence Bermudagrass 98100 100 100 100 98 75 95 98 98 98 95 98 100 Blackgrass 0 5 0 0 5 30 0 05 0 5 0 0 0 Bromegrass, Downy 5 5 0 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 1065 10 0 10 10 20 0 0 10 0 15 — 10 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0Crabgrass, Large 100 100 95 98 98 98 98 80 100 98 95 98 98 100 Cupgrass,Woolly 65 85 0 50 20 65 0 5 0 0 60 0 55 45 Foxtail, Giant 25 100 0 75 7560 15 20 0 35 75 45 55 90 Foxtail, Green 45 98 0 20 70 90 40 10 — 0 30 —25 85 Galium 70 0 20 60 30 95 98 0 0 30 0 85 70 0 Goosegrass 100 100 9895 100 100 98 98 100 98 90 90 98 100 Johnsongrass 90 60 0 55 80 80 10 055 55 85 0 75 85 Kochia — — — — — 60 85 100 100 45 85 80 95 45Lambsquarters 100 100 98 98 98 100 98 100 100 98 98 98 98 100Morningglory 45 25 45 45 55 55 45 0 0 0 25 15 65 0 Nightshade 98 100 10098 98 100 98 98 98 95 98 95 100 98 Nutsedge, Yellow 80 90 45 85 75 85 9045 25 0 85 65 85 0 Oat, Wild 5 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100 10098 100 100 100 100 100 100 85 98 98 100 100 Ragweed 85 85 85 70 85 90 7545 70 75 45 35 80 65 Russian Thistle — — — — — — — — — — — — 80 100Ryegrass, Italian 0 0 0 0 0 20 5 0 0 0 0 0 0 0 Soybean 55 80 15 80 85 00 80 5 — — — — — Sunflower 70 65 60 65 65 70 60 10 20 0 0 35 75 5Surinam Grass 95 100 0 98 85 85 0 25 55 85 90 15 55 100 Velvetleaf 98 98100 98 95 100 98 95 100 95 95 90 100 85 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 00 Compounds 125 g ai/ha 72 73 74 75 77 81 113 119 120 193 217 218 219220 Preemergence Bermudagrass 98 98 100 100 100 100 100 100 100 95 100100 100 98 Blackgrass 0 0 0 5 0 35 0 50 50 30 0 0 40 20 Bromegrass,Downy 0 5 0 0 0 0 10 55 30 5 0 0 10 0 Cocklebur 70 60 70 75 10 75 90 7060 — 85 90 — — Corn 0 0 0 0 0 50 0 50 25 5 0 0 0 0 Crabgrass, Large 100100 100 100 98 100 100 100 100 100 100 65 100 80 Cupgrass, Woolly 45 550 55 0 75 85 95 75 80 65 65 20 10 Foxtail, Giant 10 75 5 80 5 85 60 9598 70 75 20 10 0 Foxtail, Green 50 30 0 50 0 100 60 100 100 50 0 80 90 —Galium 85 80 40 95 85 100 85 90 95 100 70 95 98 90 Goosegrass 100 100100 100 98 100 100 100 100 100 100 98 100 98 Johnsongrass 0 98 0 65 0 9060 95 80 15 20 20 65 0 Kochia 85 80 85 90 90 65 85 55 50 80 — — — —Lambsquarters 98 100 98 100 100 98 100 100 100 100 100 100 100 100Morningglory 65 45 75 75 75 80 — 95 90 95 0 15 15 0 Nightshade 98 98 9898 98 98 100 98 95 100 100 100 100 98 Nutsedge, Yellow 75 65 65 90 90 9590 98 98 70 70 90 85 60 Oat, Wild 0 0 5 0 0 0 20 50 65 30 0 0 5 0Pigweed 100 100 100 100 100 100 100 100 100 100 100 100 100 100 Ragweed80 75 98 95 90 90 95 95 95 100 90 98 85 80 Russian Thistle 80 — 90 — —100 — 100 80 100 — — — — Ryegrass, Italian 0 0 0 0 0 0 5 100 100 25 5 55 0 Soybean — — — — — — 85 80 80 60 0 80 65 0 Sunflower 65 70 70 75 7585 90 70 85 80 85 90 80 70 Surinam Grass 75 100 85 60 75 100 95 100 10030 85 98 45 45 Velvetleaf 100 100 100 100 100 100 100 100 100 100 100 9090 90 Wheat 0 5 0 0 0 0 10 30 25 10 0 0 0 0 Compounds 125 g ai/ha 243244 245 255 Preemergence Bermudagrass 100 100 100 100 Blackgrass 70 6030 40 Bromegrass, Downy 60 5 0 0 Cocklebur 95 100 98 — Corn 85 60 25 0Crabgrass, Large 100 100 100 100 Cupgrass, Woolly 95 95 80 75 Foxtail,Giant 95 100 90 55 Foxtail, Green 100 90 75 80 Galium 98 98 95 60Goosegrass 100 100 100 100 Johnsongrass 95 100 80 75 Kochia 90 95 98 —Lambsquarters 100 100 100 100 Morningglory 98 98 65 65 Nightshade 98 100100 100 Nutsedge, Yellow 90 80 65 40 Oat, Wild 85 10 30 60 Pigweed 100100 100 100 Ragweed 98 100 100 85 Russian Thistle 100 — — — Ryegrass,Italian 45 5 0 10 Soybean 85 90 55 15 Sunflower 95 85 80 75 SurinamGrass 100 100 100 95 Velvetleaf 100 100 100 98 Wheat 70 5 5 0 Compounds62 g ai/ha 2 3 7 9 10 11 12 14 24 26 27 29 33 34 PreemergenceBermudagrass 100 70 0 100 80 100 100 75 100 70 98 100 100 100 Blackgrass0 0 0 0 0 5 0 0 0 0 0 5 0 5 Bromegrass, Downy 0 0 0 0 0 0 0 0 0 0 0 0 00 Cocklebur 65 10 0 25 15 75 80 85 — 40 85 80 80 55 Corn 0 0 0 0 0 0 0 00 0 0 0 0 0 Crabgrass, Large 100 70 0 90 0 100 90 50 98 40 80 100 98 100Cupgrass, Woolly 15 0 0 15 10 0 10 5 70 5 0 10 50 100 Foxtail, Giant 200 0 15 0 35 20 10 85 10 5 50 45 55 Foxtail, Green 5 0 0 0 0 25 0 0 40 030 40 45 70 Galium — 5 0 40 10 50 50 0 0 50 50 80 10 50 Goosegrass 10070 25 98 75 95 95 85 98 80 98 100 85 100 Johnsongrass 65 0 0 85 10 55 030 85 10 5 5 0 75 Kochia 100 — 100 100 50 100 100 100 100 100 100 100 —— Lambsquarters 100 — 100 100 100 100 100 100 100 100 100 100 100 100Morningglory 20 100 0 40 0 0 55 100 100 100 100 100 15 0 Nightshade 100— 90 100 100 100 100 98 98 100 98 90 100 95 Nutsedge, Yellow 40 10 10 450 55 60 30 50 50 20 30 45 45 Oat, Wild 5 0 0 0 0 0 0 0 0 0 0 0 0 10Pigweed 100 — 100 100 100 100 100 98 100 100 100 100 100 100 Ragweed 8565 0 90 100 100 98 90 90 85 85 90 85 80 Russian Thistle — — — — — — — —— — — — — — Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 60 300 10 60 45 65 — 60 60 70 85 60 45 Sunflower 70 70 0 85 80 85 98 85 90 9075 85 75 70 Surinam Grass 20 0 0 45 10 25 60 5 75 5 20 20 65 60Velvetleaf 90 90 85 100 100 100 100 98 100 90 85 90 90 85 Wheat 0 0 0 0— 0 0 0 0 0 0 0 0 0 Compounds 62 g ai/ha 36 37 38 39 40 42 44 45 46 4748 49 50 51 Preemergence Bermudagrass 100 80 100 100 100 100 100 100 —100 100 — 100 98 Blackgrass 25 0 5 0 0 0 30 0 0 5 0 0 0 0 Bromegrass,Downy 0 0 0 0 0 0 0 0 0 5 0 0 0 0 Cocklebur — — 10 — — 0 — — 0 0 0 20 750 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 90 0 90 95 98 85 7595 75 95 90 95 100 98 Cupgrass, Woolly 0 0 10 0 50 0 45 45 45 45 10 0 535 Foxtail, Giant 20 0 40 45 65 0 45 0 0 70 75 0 75 45 Foxtail, Green 800 30 — 85 65 98 80 0 80 60 0 50 50 Galium 80 10 40 80 70 0 65 40 0 50 6080 95 75 Goosegrass 90 0 100 100 98 95 98 100 95 100 100 95 98 100Johnsongrass 65 0 80 60 80 0 75 45 10 75 45 0 20 5 Kochia — — — — — — —— — — — — — — Lambsquarters 100 98 98 100 100 100 100 100 90 100 100 95100 98 Morningglory 0 0 0 0 0 0 0 — 0 — 100 80 0 20 Nightshade 95 40 95100 98 100 98 100 95 100 100 98 100 98 Nutsedge, Yellow 0 0 60 0 45 3560 10 55 45 20 60 85 70 Oat, Wild 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed100 100 100 100 100 100 98 95 85 100 100 100 100 100 Ragweed 75 10 70 4575 20 90 80 100 80 85 75 95 70 Russian Thistle — — — — — — — — — — — — —— Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 00 0 0 80 0 0 Sunflower 0 0 0 5 55 0 70 0 0 65 75 75 75 70 Surinam Grass95 45 60 10 75 5 85 60 5 98 90 — 95 98 Velvetleaf 85 0 60 45 85 80 90 6545 90 95 100 85 85 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 62 gai/ha 52 53 55 56 58 59 61 62 63 64 66 67 68 69 PreemergenceBermudagrass 98 100 98 100 98 98 75 75 98 85 80 90 98 100 Blackgrass 0 50 0 0 0 0 0 0 0 0 0 0 0 Bromegrass, Downy 5 0 0 0 0 0 0 0 0 0 0 0 0 0Cocklebur 0 20 10 0 0 0 10 0 0 0 0 0 10 0 Corn 0 0 0 0 0 0 0 — 0 0 0 0 00 Crabgrass, Large 98 100 60 85 98 95 85 50 85 75 85 65 95 100 Cupgrass,Woolly 10 55 0 20 10 65 0 0 0 0 40 0 20 0 Foxtail, Giant 15 85 0 40 20 00 0 0 25 20 0 20 75 Foxtail, Green 30 60 0 20 5 70 0 0 — 0 5 30 5 70Galium 0 0 0 0 0 90 70 0 0 0 0 35 70 — Goosegrass 100 100 95 95 98 98 9895 98 40 75 85 95 100 Johnsongrass 75 55 0 45 20 — 0 0 0 0 55 0 5 45Kochia — — — — — 45 70 100 100 0 80 70 80 20 Lambsquarters 100 100 98 9898 100 98 98 98 98 98 98 98 100 Morningglory 0 20 0 0 0 0 0 0 0 0 20 1555 0 Nightshade 95 98 98 98 98 98 95 95 95 85 95 95 98 98 Nutsedge,Yellow 25 80 45 80 75 65 70 25 15 0 30 65 70 0 Oat, Wild 5 0 0 0 0 0 0 00 0 0 0 0 0 Pigweed 100 98 95 100 98 100 100 98 98 75 98 98 98 100Ragweed 80 75 65 65 75 90 75 20 65 50 0 25 75 65 Russian Thistle — — — —— — — — — 0 0 — — 100 Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0Soybean 0 70 0 — — 0 0 80 0 — — — — — Sunflower 10 55 60 60 55 65 45 1015 0 0 20 60 0 Surinam Grass 25 85 0 95 65 75 0 20 0 85 80 10 50 100Velvetleaf 98 98 98 90 80 90 85 75 90 75 80 85 100 70 Wheat 0 0 0 0 0 00 0 0 0 0 0 0 0 Compounds 62 g ai/ha 72 73 74 75 77 81 113 119 120 193217 218 219 220 Preemergence Bermudagrass 98 98 98 100 100 100 95 100100 95 100 100 100 98 Blackgrass 0 0 0 0 0 0 0 30 50 0 0 0 35 20Bromegrass, Downy 0 5 0 0 0 0 10 50 30 5 0 0 0 0 Cocklebur 50 0 45 20 010 75 — 35 75 — 0 75 0 Corn 0 0 0 0 0 40 0 40 — 0 0 0 0 0 Crabgrass,Large 100 98 98 100 98 100 98 100 100 100 100 20 98 75 Cupgrass, Woolly0 20 0 — 0 55 50 75 70 70 5 0 10 0 Foxtail, Giant 5 70 0 25 0 75 40 8598 65 40 0 0 0 Foxtail, Green 0 30 0 50 0 90 40 100 98 50 0 30 70 90Galium 85 30 30 85 20 100 70 85 90 100 10 80 85 50 Goosegrass 98 98 98100 95 98 90 100 100 100 98 60 100 95 Johnsongrass 0 0 0 10 0 80 5 85 700 5 0 15 0 Kochia 75 — — 90 90 55 80 0 20 70 — — — — Lambsquarters 98 9898 100 98 98 100 98 100 100 100 100 100 100 Morningglory 55 0 60 60 6565 — 95 90 90 0 0 0 0 Nightshade 95 95 98 98 98 98 98 98 95 100 100 9898 90 Nutsedge, Yellow 70 65 55 80 80 75 80 95 90 65 65 75 45 0 Oat,Wild 0 0 0 0 0 0 5 45 10 5 0 0 0 0 Pigweed 98 100 98 100 100 100 98 90100 100 100 100 100 100 Ragweed 70 60 98 75 75 85 90 80 80 100 60 95 7560 Russian Thistle 30 — 80 — — 100 — 100 80 98 — — — — Ryegrass, Italian0 0 0 0 0 0 5 100 100 0 0 0 0 0 Soybean — — — — — — 65 55 70 60 0 65 0 0Sunflower 25 20 55 55 75 75 80 60 — 80 75 80 45 45 Surinam Grass 75 10080 60 20 100 80 98 100 15 75 65 10 20 Velvetleaf 100 100 100 100 100 100100 80 100 100 100 85 75 70 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds62 g ai/ha 243 244 245 255 Preemergence Bermudagrass 100 100 100 100Blackgrass 10 35 5 20 Bromegrass, Downy 40 0 0 0 Cocklebur 75 90 0 —Corn 75 25 5 0 Crabgrass, Large 100 100 100 95 Cupgrass, Woolly 95 55 7010 Foxtail, Giant 85 80 10 45 Foxtail, Green 100 45 0 80 Galium 90 65 6050 Goosegrass 100 100 100 98 Johnsongrass 95 85 75 60 Kochia 20 90 45 —Lambsquarters 100 100 100 100 Morningglory — 90 0 55 Nightshade 98 100100 90 Nutsedge, Yellow 80 60 0 25 Oat, Wild 85 5 0 0 Pigweed 98 100 95100 Ragweed 95 95 85 75 Russian Thistle 100 — — — Ryegrass, Italian 10 00 0 Soybean 75 80 10 0 Sunflower 85 80 70 60 Surinam Grass 98 100 100 85Velvetleaf 100 100 100 95 Wheat 40 0 0 0 Compounds 31 g ai/ha 2 3 7 9 1011 12 14 24 26 27 29 33 34 Preemergence Bermudagrass 98 10 0 98 45 98100 70 95 5 70 98 98 100 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 5 0 0Bromegrass, Downy 0 0 0 0 0 0 0 0 0 0 0 0 0 — Cocklebur 0 10 0 0 0 35 250 10 10 0 5 25 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 15 00 0 0 60 0 5 90 0 5 98 85 55 Cupgrass, Woolly 0 0 0 0 0 0 0 0 5 0 0 5 10100 Foxtail, Giant 15 0 0 0 0 0 0 0 30 5 0 10 10 15 Foxtail, Green 0 0 00 0 0 0 0 0 0 0 0 0 50 Galium — 0 0 0 0 5 0 0 0 0 0 50 0 10 Goosegrass85 30 10 75 0 70 85 70 85 5 80 95 80 95 Johnsongrass 60 0 0 0 0 0 0 5 200 0 0 0 20 Kochia 100 98 15 15 0 15 15 85 100 80 100 98 — —Lambsquarters 100 100 100 100 100 100 100 100 98 98 100 100 98 100Morningglory 0 100 — 0 0 0 40 100 100 100 100 100 0 0 Nightshade 98 5080 100 100 85 100 85 90 85 80 90 80 55 Nutsedge, Yellow 15 5 0 0 0 0 250 30 10 0 0 0 10 Oat, Wild — 0 0 0 0 0 0 0 0 0 0 0 0 10 Pigweed 100 85100 50 100 100 100 90 98 98 100 100 100 100 Ragweed 60 65 0 55 98 65 9070 85 65 85 80 80 75 Russian Thistle — — — — — — — — — — — — — —Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 15 0 0 0 10 25 6025 45 50 70 20 60 0 Sunflower 50 50 0 45 0 75 95 50 85 60 75 75 65 55Surinam Grass 15 0 0 0 0 0 35 0 65 0 0 0 0 5 Velvetleaf 75 50 40 98 55100 90 70 98 50 55 10 80 75 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 — Compounds31 g ai/ha 36 37 38 39 40 42 44 45 46 47 48 49 50 51 PreemergenceBermudagrass 95 10 98 85 98 90 100 98 0 100 100 — 100 95 Blackgrass 20 00 0 0 0 5 0 0 0 0 0 0 0 Bromegrass, Downy 0 0 0 0 0 0 0 0 0 0 0 0 0 0Cocklebur — 0 0 0 65 0 — — 0 — — 0 — 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0Crabgrass, Large 20 0 60 55 70 45 65 45 45 75 75 75 98 75 Cupgrass,Woolly 0 0 0 0 0 0 0 45 10 0 10 0 0 10 Foxtail, Giant 10 0 0 0 10 0 20 00 45 20 0 45 0 Foxtail, Green 35 0 20 — 0 65 0 0 0 65 60 0 50 50 Galium10 0 0 70 50 0 0 40 0 50 0 0 70 0 Goosegrass 0 0 95 85 80 50 90 80 85 9598 20 95 98 Johnsongrass 0 0 10 0 10 0 10 0 0 65 20 0 0 0 Kochia — — — —— — — — — — — — — — Lambsquarters 98 95 98 100 100 100 100 100 90 100100 95 100 95 Morningglory 0 0 0 0 0 0 0 0 0 0 0 45 0 0 Nightshade 80 090 50 65 100 95 98 95 100 100 98 100 98 Nutsedge, Yellow 0 0 10 0 10 1045 0 25 45 20 60 80 55 Oat, Wild 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Pigweed 100100 100 90 98 100 98 85 85 98 100 100 90 100 Ragweed 35 0 40 0 75 0 2045 100 45 65 70 75 65 Russian Thistle — — — — — — — — — — — — — —Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Soybean 0 0 0 0 0 0 0 0 00 0 0 0 0 Sunflower 0 0 0 0 20 0 10 0 0 65 0 60 55 20 Surinam Grass 70 040 0 40 0 65 45 0 85 80 0 75 95 Velvetleaf 65 0 55 15 80 75 75 0 0 80 7595 85 75 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Compounds 31 g ai/ha 52 53 5556 58 59 61 62 63 64 66 67 68 69 Preemergence Bermudagrass 98 — 95 98 9810 20 20 75 50 20 45 95 98 Blackgrass 0 0 0 0 0 0 0 0 0 0 0 0 0 0Bromegrass, Downy 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Cocklebur 0 10 0 0 0 0 0 00 0 0 0 0 0 Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Crabgrass, Large 60 75 1080 95 55 70 0 50 50 70 40 65 98 Cupgrass, Woolly 0 0 0 0 10 10 0 0 0 025 0 5 0 Foxtail, Giant 0 5 0 0 10 0 0 0 0 20 15 0 0 5 Foxtail, Green 060 0 0 0 — 0 0 0 0 0 0 0 — Galium 0 0 0 0 0 0 70 0 0 0 0 0 0 —Goosegrass 98 98 45 90 95 98 80 15 90 30 35 85 80 95 Johnsongrass 10 100 10 10 — 0 0 0 0 0 0 0 5 Kochia — — — — — 0 0 98 0 0 80 70 80 0Lambsquarters 98 98 95 95 85 98 90 98 98 95 98 98 98 98 Morningglory 0 00 0 0 — 0 0 0 0 0 0 0 0 Nightshade 90 98 60 85 90 95 90 10 80 55 80 7098 95 Nutsedge, Yellow 0 65 0 20 20 55 25 15 10 0 10 0 0 0 Oat, Wild 0 00 0 0 0 0 0 0 0 0 0 0 0 Pigweed 90 95 45 98 85 90 0 45 95 55 98 98 95 98Ragweed 80 65 55 20 20 75 50 0 65 0 0 25 10 65 Russian Thistle — — — — —— — — — — — 85 — 100 Ryegrass, Italian 0 0 0 0 0 0 — 0 0 0 0 0 0 0Soybean 0 0 0 20 10 — — 0 0 — — — — — Sunflower 10 15 10 0 0 55 0 0 5 00 0 0 0 Surinam Grass 10 75 0 55 40 5 0 5 0 0 35 0 45 80 Velvetleaf 8080 75 85 75 75 80 75 75 65 80 75 95 70 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0Compounds 31 g ai/ha 72 73 74 75 77 81 113 119 120 193 217 218 219 220Preemergence Bermudagrass 95 50 — 98 55 100 95 100 100 75 98 98 98 80Blackgrass 0 0 0 0 0 0 0 30 5 0 0 0 30 10 Bromegrass, Downy 0 0 0 0 0 00 0 10 0 0 0 0 0 Cocklebur 10 0 10 10 0 0 45 0 0 — — — — 0 Corn 0 0 0 00 40 0 0 0 0 0 0 0 0 Crabgrass, Large 95 85 98 98 70 100 70 100 98 10095 0 10 0 Cupgrass, Woolly 0 10 0 5 0 40 5 65 50 10 0 0 0 0 Foxtail,Giant 0 0 0 0 0 60 5 55 75 0 5 0 0 0 Foxtail, Green 0 0 0 5 0 80 10 9595 5 0 0 20 80 Galium 0 — 20 60 0 85 50 65 80 75 0 60 75 0 Goosegrass 6085 98 95 55 98 75 100 100 98 95 10 98 65 Johnsongrass 0 0 0 0 0 10 0 5035 0 0 0 0 0 Kochia 45 0 80 80 85 45 80 0 0 20 — — — — Lambsquarters 9895 98 98 98 98 98 95 100 100 95 100 100 100 Morningglory 0 0 10 0 0 — —60 0 75 0 0 0 0 Nightshade 95 75 85 95 98 98 98 90 90 100 95 98 90 65Nutsedge, Yellow 40 20 20 60 75 10 65 75 70 10 60 45 0 0 Oat, Wild 0 0 00 0 0 0 0 0 5 0 0 0 — Pigweed 98 95 98 98 100 100 98 80 95 98 95 100 100100 Ragweed 55 45 10 75 50 60 55 80 80 100 60 85 45 15 Russian Thistle 00 0 — — 100 — 100 — 90 — — — — Ryegrass, Italian 0 0 0 0 0 0 0 100 100 00 0 0 0 Soybean — — — — — — 0 10 15 40 0 0 0 — Sunflower 25 0 0 30 60 6075 40 45 70 70 75 0 0 Surinam Grass 45 85 0 40 0 98 0 90 100 0 45 10 1010 Velvetleaf 98 100 98 100 95 100 80 75 80 85 95 80 0 45 Wheat 0 0 0 00 0 0 0 0 0 0 0 0 0 Compounds 31 g ai/ha 243 244 245 255 PreemergenceBermudagrass 100 100 98 100 Blackgrass 0 35 0 0 Bromegrass, Downy 0 0 00 Cocklebur — — 0 — Corn 65 5 0 0 Crabgrass, Large 100 98 60 80Cupgrass, Woolly 75 45 50 0 Foxtail, Giant 55 60 0 15 Foxtail, Green 350 0 0 Galium 85 55 20 0 Goosegrass 98 98 95 80 Johnsongrass 70 70 65 0Kochia 15 85 0 — Lambsquarters 100 100 100 98 Morningglory — 85 0 40Nightshade 90 98 98 75 Nutsedge, Yellow 65 20 0 10 Oat, Wild 30 0 0 0Pigweed 75 100 80 100 Ragweed 85 70 75 65 Russian Thistle 100 — — —Ryegrass, Italian 0 0 0 0 Soybean 65 70 0 0 Sunflower 80 80 45 45Surinam Grass 80 75 95 65 Velvetleaf 100 100 95 80 Wheat 0 0 0 0Compounds 16 g ai/ha 2 69 Preemergence Bermudagrass 25 90 Blackgrass 0 0Bromegrass, Downy 0 0 Cocklebur 0 0 Corn 0 0 Crabgrass, Large 0 75Cupgrass, Woolly 0 0 Foxtail, Giant 0 0 Foxtail, Green 0 — Goosegrass 055 Johnsongrass 0 0 Kochia 0 — Lambsquarters 100 95 Morningglory 0 0Nightshade 55 80 Nutsedge, Yellow 0 0 Oat, Wild 0 0 Pigweed 98 95Ragweed 25 40 Russian Thistle — 100 Ryegrass, Italian 0 — Soybean 0 —Sunflower 0 0 Surinam Grass 0 75 Velvetleaf 0 0 Wheat 0 0

Test C

Seeds of plant species selected from bluegrass (annual bluegrass, Poaannua), blackgrass (Alopecurus myosuroides), canarygrass (Phalarisminor), chickweed (common chickweed, Stellaria media), galium (catchweedbedstraw, Galium aparine), bromegrass (downy bromegrass, Bromustectorum), field poppy (Papaver rhoeas), field violet (Viola arvensis),green foxtail (Setaria viridis), deadnettle (henbit deadnettle, Lamiumamplexicaule), Italian ryegrass (Lolium multiflorum), kochia (Kochiascoparia), lambsquarters (Chenopodium album), oilseed rape (Brassicanapus), pigweed (Amaranthus retroflexus), Russian thistle (Salsolaiberica), spring barley (Hordeum vulgare), spring wheat (Triticumaestivum), buckwheat (wild buckwheat, Polygonum convolvulus), wildmustard (Sinapis arvensis), wild oat (Avena fatua), wild radish(Raphanus raphanistrum), windgrass (Apera spica-venti), winter barley(Hordeum vulgare), and winter wheat (Triticum aestivum) were planted andtreated postemergence with test chemicals formulated in a non-phytotoxicsolvent mixture which included a surfactant. Plants ranged in heightfrom 2 to 18 cm (1- to 4-leaf stage).

Treated plants and controls were maintained in a controlled growthenvironment for 14 days after which time all test plants were visuallyevaluated and compared to controls. Plant response ratings, summarizedin Table C, are based on a scale of 0 to 100 where 0 is no effect and100 is complete control. A dash (-) response means no test result.

TABLE C Compounds 125 g ai/ha 2 4 8 11 12 33 Postemergence Barley,Spring 0 15 30 30 0 0 Barley, Winter 30 35 40 60 0 5 Blackgrass 30 40 3535 40 35 Bluegrass 65 50 75 80 40 40 Bromegrass, Downy 50 40 40 65 20 20Buckwheat, Wild 70 100 65 80 50 75 Canarygrass — 90 10 10 — 5 Chickweed— 100 98 100 — 100 Deadnettle 100 100 100 100 100 100 Field Poppy — 5060 70 — 98 Field Violet 50 60 65 35 40 95 Foxtail, Green 95 95 98 95 9095 Galium 70 90 90 65 80 60 Kochia 98 95 90 98 75 70 Lambsquarters 98100 100 100 95 100 Mustard, Wild — 100 98 100 95 100 Oat, Wild 25 50 3070 15 10 Oilseed Rape 90 100 100 100 95 100 Pigweed 90 100 98 98 75 98Radish, Wild 95 95 100 95 90 98 Russian Thistle 95 95 95 95 70 90Ryegrass, Italian 30 15 35 30 0 10 Wheat, Spring 0 20 20 40 0 10 Wheat,Winter 30 20 30 35 10 5 Windgrass 40 95 60 95 50 40 Compounds 62 g ai/ha2 8 11 12 33 Postemergence Barley, Spring 0 20 20 0 0 Barley, Winter 1020 40 0 0 Blackgrass 20 35 35 30 35 Bluegrass 25 50 65 30 15 Bromegrass,Downy 30 35 65 15 15 Buckwheat, Wild 40 65 80 50 75 Canarygrass — 10 10— 5 Chickweed — 95 98 — 98 Deadnettle 100 98 100 100 98 Field Poppy — 4040 — 90 Field Violet 40 65 35 40 95 Foxtail, Green 95 95 95 80 95 Galium50 90 65 60 50 Kochia 75 85 95 35 60 Lambsquarters 80 98 98 80 100Mustard, Wild 98 98 98 95 98 Oat, Wild 25 30 50 15 5 Oilseed Rape 70 9898 80 100 Pigweed 75 98 95 75 95 Radish, Wild 95 98 95 90 95 RussianThistle 70 95 95 60 90 Ryegrass, Italian 15 20 30 0 10 Wheat, Spring 0 535 0 10 Wheat, Winter 0 25 30 0 5 Windgrass 25 20 85 — 25 Compounds 31 gai/ha 2 4 8 11 12 33 Postemergence Barley, Spring 0 10 10 15 0 0 Barley,Winter 0 5 20 20 0 0 Blackgrass 0 20 30 20 20 5 Bluegrass 25 35 25 35 200 Bromegrass, Downy 20 35 25 50 10 10 Buckwheat, Wild 20 95 65 70 15 65Canarygrass — 0 5 5 — 0 Chickweed — 98 95 95 — 90 Deadnettle 95 98 95 98100 98 Field Poppy — 30 20 30 — 80 Field Violet 40 40 65 0 35 90Foxtail, Green 75 70 95 95 60 95 Galium 30 65 75 30 50 40 Kochia 70 9070 90 10 50 Lambsquarters 75 100 98 98 80 98 Mustard, Wild 98 98 95 9895 98 Oat, Wild 15 20 20 25 15 0 Oilseed Rape 60 90 90 95 70 98 Pigweed40 95 95 95 65 95 Radish, Wild 80 80 95 95 80 95 Russian Thistle 60 7090 80 60 80 Ryegrass, Italian 0 10 0 5 0 0 Wheat, Spring 0 15 5 20 0 10Wheat, Winter 0 0 10 30 0 0 Windgrass 20 35 10 70 20 20 Compounds 16 gai/ha 2 8 11 12 33 Postemergence Barley, Spring 0 0 0 0 0 Barley, Winter0 0 0 0 0 Blackgrass 0 20 20 0 0 Bluegrass 0 5 — 10 0 Bromegrass, Downy10 10 30 0 0 Buckwheat, Wild 15 65 65 10 60 Canarygrass — 0 5 — 0Chickweed — 95 95 — 90 Deadnettle 95 85 95 100 95 Field Poppy — 0 20 —80 Field Violet 0 10 0 35 65 Foxtail, Green 65 95 95 50 80 Galium 5 5020 5 35 Kochia 65 65 70 0 35 Lambsquarters 70 98 98 70 98 Mustard, Wild98 — 98 80 98 Oat, Wild 0 20 25 0 0 Oilseed Rape 60 80 90 50 90 Pigweed35 95 75 65 75 Radish, Wild 65 85 95 60 90 Russian Thistle 35 90 80 6080 Ryegrass, Italian 0 0 0 0 0 Wheat, Spring 0 5 5 0 10 Wheat, Winter 010 0 0 0 Windgrass 5 0 60 5 0 Compounds 2 12 Preemergence 125 g ai/haBarley, Spring 0 0 Barley, Winter 0 0 Blackgrass 0 0 Bluegrass 0 35Bromegrass, Downy 0 0 Buckwheat, Wild 0 40 Canarygrass 10 20 Chickweed98 50 Deadnettle 98 100 Field Poppy 100 98 Field Violet 0 0 Foxtail,Green 0 0 Galium 50 35 Kochia 90 25 Lambsquarters 100 100 Mustard, Wild35 — Oat, Wild 0 0 Oilseed Rape 65 40 Pigweed 85 65 Radish, Wild 0 0Ryegrass, Italian 0 0 Wheat, Spring 0 0 Wheat, Winter 0 0 Windgrass 2540 62 g ai/ha Barley, Spring 0 0 Barley, Winter 0 0 Blackgrass 0 0Bluegrass 0 20 Bromegrass, Downy 0 0 Buckwheat, Wild 0 0 Canarygrass 0 —Chickweed 98 — Deadnettle 95 90 Field Poppy 95 98 Field Violet 0 0Foxtail, Green 0 0 Galium 0 35 Kochia 30 5 Lambsquarters 0 70 Mustard,Wild 5 5 Oat, Wild 0 0 Oilseed Rape 35 30 Pigweed 65 50 Radish, Wild 0 0Russian Thistle 0 0 Ryegrass, Italian 0 0 Wheat, Spring 0 0 Wheat,Winter 0 0 Windgrass 25 40 31 g ai/ha Barley, Spring 0 0 Barley, Winter0 0 Blackgrass 0 0 Bluegrass 0 0 Bromegrass, Downy 0 0 Buckwheat, Wild 00 Canarygrass 0 — Chickweed 98 — Deadnettle 75 50 Field Poppy 75 80Field Violet 0 0 Foxtail, Green 0 0 Galium — 0 Kochia 5 5 Lambsquarters0 20 Mustard, Wild 0 — Oat, Wild 0 0 Oilseed Rape 20 20 Pigweed 20 0Radish, Wild 0 0 Russian Thistle 0 0 Ryegrass, Italian 0 0 Wheat, Spring0 0 Wheat, Winter 0 0 Windgrass 15 20 16 g ai/ha Barley, Spring 0 0Barley, Winter 0 0 Blackgrass 0 0 Bluegrass 0 0 Bromegrass, Downy 0 0Buckwheat, Wild 0 0 Canarygrass 0 — Chickweed 75 — Deadnettle 0 35 FieldPoppy — 50 Field Violet 0 0 Foxtail, Green 0 0 Galium — 0 Kochia 5 5Lambsquarters 0 0 Mustard, Wild 0 0 Oat, Wild 0 0 Oilseed Rape 0 0Pigweed 0 0 Radish, Wild 0 0 Russian Thistle 0 0 Ryegrass, Italian 0 0Wheat, Spring 0 0 Wheat, Winter 0 0 Windgrass 0 20

Test D

Seeds of plant species selected from bermudagrass (Cynodon dactylon),Surinam grass (Brachiaria decumbens), large crabgrass (Digitariasanguinalis), green foxtail (Setaria viridis), goosegrass (Eleusineindica), johnsongrass (Sorghum halepense), kochia (Kochia scoparia),morning glory (pitted morning glory, Ipomoea lacunosa), nutsedge (purplenutsedge, Cyperus rotundus), ragweed (common ragweed, Ambrosia elatior),black mustard (Brassica nigra), guineagrass (Panicum maximum),dallisgrass (Paspalum dilatatum), barnyardgrass (Echinochloacrus-galli), sandbur (southern sandbur, Cenchrus echinatus), sowthistle(common sowthistle, Sonchus oleraceous), prickly sida (Sida spinosa),Italian ryegrass (Lolium multiflorum), purslane (common purslane,Portulaca oleracea), signalgrass (broadleaf signalgrass, Brachiariaplatyphylla), groundsel (common groundsel, Senecio vulgaris), chickweed(common chickweed, Stellaria media), dayflower (Virginia (VA) dayflower,Commelina virginica), bluegrass (annual bluegrass, Poa annua), nakedcrabgrass (Digitaria nuda), itchgrass (Rottboellia cochinchinensis),quackgrass (Elytrigia repens), field bindweed (Convolvulus arvensis),spanishneedles (Bidens bipinnata), mallow (common mallow, Malvasylvestris) and Russian thistle (Salsola kali), were planted into ablend of loam soil and sand and treated preemergence with test chemicalsformulated in a non-phytotoxic solvent mixture which included asurfactant. At the same time, plants from these weed species weretreated with postemergence applications of the test chemicals formulatedin the same manner. Plants ranged in height from 2 to 18 cm (1- to4-leaf stage) for postemergence treatments.

Treated plants and controls were maintained in a greenhouse for 14 to 21days, after which time all species were visually evaluated and comparedto controls. Plant response ratings, summarized in Table D, are based ona scale of 0 to 100 where 0 is no effect and 100 is complete control. Adash (-) response means no test result.

TABLE D Compounds 250 g ai/ha 226 235 238 240 243 244 245 PostemergenceBarnyardgrass 95 95 95 95 90 90 90 Bermudagrass 98 95 95 95 95 95 80Black Mustard 85 98 98 98 98 98 98 Bluegrass 30 50 40 35 35 20 35Chickweed 85 70 50 70 70 60 50 Crabgrass, Large 85 80 80 70 85 75 75Crabgrass, Naked 75 — — — — — — Dallisgrass 35 80 75 75 90 80 85Dayflower, VA 65 75 75 75 75 70 75 Field Bindweed 80 70 50 70 70 70 70Foxtail, Green 98 98 95 98 98 100 95 Goosegrass 75 75 75 80 75 70 75Groundsel 100 100 100 100 100 100 100 Guineagrass 80 75 75 80 85 75 85Itchgrass 90 90 80 80 85 75 75 Johnsongrass 90 85 80 95 75 75 75 Kochia70 85 75 70 75 65 75 Mallow 65 70 60 60 70 70 70 Morningglory 80 95 9095 85 75 80 Nutsedge, Purple 5 40 20 20 50 35 20 Prickly Sida 75 75 6575 80 60 70 Purslane 70 70 60 50 50 50 30 Quackgrass 35 70 40 50 75 6565 Ragweed 98 80 75 90 75 85 75 Russian Thistle 70 60 50 35 60 65 70Ryegrass, Italian 15 35 5 35 65 60 50 Sandbur 75 75 85 90 80 75 75Signalgrass 65 95 65 85 95 35 75 Sowthistle 98 98 95 98 98 100 95Spanishneedles 80 85 75 75 70 75 75 Surinam Grass 90 85 85 95 85 80 75Compounds 125 g ai/ha 47 51 52 59 66 85 87 113 128 226 228 233 235 238Postemergence Barnyardgrass 70 70 80 75 75 70 70 80 90 95 80 85 95 85Bermudagrass 90 85 80 80 65 90 85 80 90 95 70 70 95 95 Black Mustard 100100 98 98 98 85 100 100 95 80 50 100 98 98 Bluegrass 0 0 35 5 0 5 0 0 010 5 0 35 20 Chickweed 65 70 100 — 95 100 100 — 70 35 75 60 60 40Crabgrass, Large 65 35 70 70 35 75 75 70 70 75 75 60 75 75 Crabgrass,Naked 65 65 95 70 70 80 75 75 75 70 — 70 — — Dallisgrass 15 70 75 50 6080 75 70 60 30 5 35 80 70 Dayflower, VA 30 20 60 — 30 80 70 60 70 — 8560 75 70 Field Bindweed 65 60 70 60 0 75 40 — 65 70 70 70 65 — Foxtail,Green 95 65 95 35 80 65 60 90 70 80 80 35 98 80 Goosegrass 65 65 80 6575 75 65 65 70 70 70 65 75 75 Groundsel 100 100 100 100 80 100 100 100100 95 100 100 100 100 Guineagrass 30 50 75 20 30 60 30 70 35 80 15 5075 65 Itchgrass 10 80 65 75 40 70 30 70 65 70 65 80 80 75 Johnsongrass65 70 — 60 60 80 60 75 65 80 70 50 85 75 Kochia 30 20 40 50 40 60 60 5040 70 75 35 70 65 Mallow 65 20 75 40 60 75 70 20 40 50 65 0 70 50Morningglory 50 65 70 50 90 90 50 90 70 70 50 70 95 80 Nutsedge, Purple20 20 40 25 30 65 50 50 50 0 15 0 30 20 Prickly Sida 90 75 90 70 98 9895 70 80 70 65 60 70 50 Purslane 30 35 75 50 75 90 35 75 50 65 35 40 6060 Quackgrass 5 0 20 0 5 20 5 30 5 20 5 25 40 30 Ragweed 95 85 95 80 5100 98 80 90 90 75 98 80 75 Russian Thistle — — — 65 — — 35 20 — 40 6510 50 50 Ryegrass, Italian 30 0 35 5 15 20 5 50 5 0 5 5 5 5 Sandbur 3560 80 25 90 95 35 60 35 75 5 75 75 75 Signalgrass 20 50 90 20 30 75 6075 35 65 20 35 90 60 Sowthistle 100 100 100 100 90 100 100 100 100 98 98100 98 95 Spanishneedles 70 70 80 70 80 95 70 60 65 75 70 60 80 70Surinam Grass 70 80 90 60 90 85 40 — 50 90 70 60 75 75 Compounds 125 gai/ha 240 243 244 245 Postemergence Barnyardgrass 95 80 85 85Bermudagrass 95 95 95 80 Black Mustard 98 98 95 98 Bluegrass 35 35 10 35Chickweed 60 60 40 50 Crabgrass, Large 65 85 75 75 Crabgrass, Naked — —— — Dallisgrass 75 90 75 80 Dayflower, VA 70 70 65 65 Field Bindweed 7070 65 60 Foxtail, Green 98 90 95 95 Goosegrass 80 70 70 70 Groundsel 100100 100 100 Guineagrass 80 75 75 75 Itchgrass 80 75 75 75 Johnsongrass95 70 75 75 Kochia 65 70 50 70 Mallow 60 70 60 50 Morningglory 90 85 7580 Nutsedge, Purple 5 25 10 5 Prickly Sida 75 70 40 50 Purslane — 50 5030 Quackgrass 35 70 50 40 Ragweed 80 75 80 75 Russian Thistle — 30 60 60Ryegrass, Italian 35 30 35 20 Sandbur 90 75 75 75 Signalgrass 75 75 2550 Sowthistle 98 95 100 95 Spanishneedles 75 70 75 70 Surinam Grass 9575 80 75 Compounds 62 g ai/ha 47 51 52 59 66 85 87 113 128 226 233 235238 240 Postemergence Barnyardgrass 70 70 75 60 70 65 60 80 70 85 85 8080 95 Bermudagrass 70 80 75 70 65 80 70 80 80 95 70 95 90 95 BlackMustard 100 — 98 65 50 75 100 100 95 80 50 80 95 80 Bluegrass 0 0 35 0 05 0 0 0 10 0 20 5 35 Chickweed — — 98 70 35 100 75 — 65 35 — 30 35 50Crabgrass, Large 60 35 70 50 25 75 70 70 60 75 50 75 70 65 Crabgrass,Naked 35 — 95 50 65 75 70 70 70 65 60 — — — Dallisgrass 15 30 70 20 3565 50 60 30 20 10 75 65 70 Dayflower, VA 20 10 30 60 0 60 60 60 60 50 3570 65 60 Field Bindweed 50 20 70 30 0 75 25 65 65 70 50 65 50 70Foxtail, Green 50 40 85 20 65 35 35 70 65 70 30 95 80 98 Goosegrass 6565 75 50 65 75 65 65 65 70 60 75 70 70 Groundsel 100 100 100 100 80 100100 100 100 90 90 100 100 100 Guineagrass 20 30 75 20 10 35 20 50 30 8040 75 50 65 Itchgrass 5 40 65 15 35 65 30 65 40 70 70 75 70 75Johnsongrass 35 60 85 40 50 80 40 65 50 80 50 70 70 90 Kochia 20 5 0 2025 20 35 50 30 60 30 60 50 65 Mallow 65 0 65 5 60 70 70 0 40 50 0 50 3540 Morningglory — 20 70 50 90 75 40 90 70 70 70 75 80 80 Nutsedge,Purple 10 15 35 20 20 50 20 35 35 0 0 5 10 5 Prickly Sida 80 65 80 70 9895 80 70 65 65 50 65 30 65 Purslane 30 35 65 35 75 90 35 50 30 50 30 6060 35 Quackgrass 0 0 15 0 5 15 0 20 0 0 10 30 5 30 Ragweed 80 80 95 — 080 95 75 90 90 75 70 75 75 Russian Thistle 20 — — — — — — 20 20 — — 3040 35 Ryegrass, Italian 20 0 15 5 0 15 0 35 0 0 5 5 5 35 Sandbur 20 2575 5 35 65 20 60 5 75 70 75 75 70 Signalgrass 15 50 80 10 30 60 60 60 3540 25 90 35 75 Sowthistle 100 100 98 100 70 100 98 100 100 98 — 98 95 98Spanishneedles 65 60 80 70 80 90 60 50 50 75 50 70 70 65 Surinam Grass60 70 80 50 90 75 40 80 30 70 50 75 75 70 Compounds 62 g ai/ha 243 244245 Postemergence Barnyardgrass 80 80 85 Bermudagrass 85 80 80 BlackMustard 75 75 95 Bluegrass 5 10 20 Chickweed 50 20 25 Crabgrass, Large80 75 70 Crabgrass, Naked — — — Dallisgrass 80 75 75 Dayflower, VA 65 5035 Field Bindweed 70 35 50 Foxtail, Green 85 90 90 Goosegrass 70 60 70Groundsel 100 100 100 Guineagrass 75 75 75 Itchgrass 75 70 70Johnsongrass 70 70 75 Kochia 60 50 65 Mallow 60 50 50 Morningglory 85 7075 Nutsedge, Purple 25 0 5 Prickly Sida 65 35 50 Purslane 50 50 5Quackgrass 40 40 35 Ragweed 70 70 75 Russian Thistle 30 40 60 Ryegrass,Italian 20 15 5 Sandbur 75 70 70 Signalgrass 75 20 40 Sowthistle 90 9595 Spanishneedles 65 65 70 Surinam Grass 75 75 75 Compounds 31 g ai/ha47 51 52 59 66 85 87 113 128 226 228 233 235 238 PostemergenceBarnyardgrass 70 70 75 60 65 50 50 75 70 85 20 75 80 75 Bermudagrass 5075 75 40 50 75 65 70 70 90 70 70 80 80 Black Mustard 100 95 90 40 20 6065 — 95 65 20 50 80 80 Bluegrass 0 0 25 0 0 0 0 0 0 0 0 0 5 0 Chickweed65 — 90 70 — 80 75 70 — 20 35 50 5 30 Crabgrass, Large 50 35 70 35 25 6065 60 50 65 65 40 70 50 Crabgrass, Naked 35 50 75 30 50 50 60 65 65 60 —50 — — Dallisgrass 10 20 65 10 35 25 25 10 20 15 0 10 70 10 Dayflower,VA 15 10 5 — 0 30 35 40 50 50 35 35 60 35 Field Bindweed 40 5 70 5 0 7515 65 50 70 65 50 60 35 Foxtail, Green 35 20 70 5 35 25 30 60 40 65 7010 70 75 Goosegrass 65 65 75 20 50 65 35 50 40 70 50 50 75 50 Groundsel100 98 100 90 60 100 98 90 100 80 100 50 100 100 Guineagrass 20 30 70 105 20 20 25 30 80 0 30 75 25 Itchgrass 5 20 50 15 15 35 0 10 40 50 40 6570 70 Johnsongrass 15 35 75 35 20 50 30 40 40 50 65 35 70 60 Kochia 10 50 5 25 10 35 40 30 60 65 20 20 20 Mallow 50 0 65 5 30 65 60 0 5 35 40 010 25 Morningglory 5 20 65 40 70 70 40 60 65 50 50 60 75 70 Nutsedge,Purple 0 0 20 0 5 30 10 10 10 0 5 0 5 5 Prickly Sida 70 50 65 40 98 9580 60 60 40 40 50 65 30 Purslane 20 20 65 35 50 80 25 30 30 50 — 30 6060 Quackgrass 0 0 10 0 5 0 0 0 0 0 0 0 5 5 Ragweed 75 75 95 70 0 80 8070 75 80 75 75 70 70 Russian Thistle — — — — — — — 0 0 — 20 — 30 30Ryegrass, Italian 10 0 0 0 0 0 0 20 0 0 0 0 5 5 Sandbur 5 25 65 5 35 505 10 5 60 5 65 75 50 Signalgrass 5 35 60 5 10 35 30 40 30 35 15 5 65 20Sowthistle 100 98 95 100 65 100 98 95 100 90 95 100 98 95 Spanishneedles40 50 75 50 70 75 60 35 50 70 65 35 65 65 Surinam Grass 50 60 65 35 6075 40 75 25 65 5 — 75 75 Compounds 31 g ai/ha 240 243 244 245Postemergence Barnyardgrass 80 75 80 80 Bermudagrass 85 75 80 80 BlackMustard 70 50 50 75 Bluegrass 5 5 0 5 Chickweed 25 35 15 5 Crabgrass,Large 40 75 70 70 Crabgrass, Naked — — — — Dallisgrass 5 75 40 65Dayflower, VA 35 35 30 20 Field Bindweed 60 65 20 50 Foxtail, Green 9580 75 85 Goosegrass 70 65 50 70 Groundsel 100 98 100 95 Guineagrass 4070 70 75 Itchgrass 75 75 60 70 Johnsongrass 70 70 70 70 Kochia 20 50 2550 Mallow 10 50 50 35 Morningglory 65 75 65 70 Nutsedge, Purple 0 20 0 5Prickly Sida 35 60 25 30 Purslane 0 35 25 0 Quackgrass 25 35 20 20Ragweed 70 65 65 70 Russian Thistle 35 20 20 25 Ryegrass, Italian 0 0 55 Sandbur 70 75 70 65 Signalgrass 20 50 20 10 Sowthistle 98 90 75 95Spanishneedles 65 60 65 65 Surinam Grass 70 75 75 75 Compounds 16 gai/ha 47 51 52 59 66 85 87 113 128 233 Postemergence Barnyardgrass 70 6575 40 35 30 35 65 35 65 Bermudagrass 50 65 75 35 5 65 65 65 70 70 BlackMustard 95 70 65 10 0 35 40 100 95 20 Bluegrass 0 0 15 0 0 0 0 0 0 0Chickweed 50 — 75 — — — 75 — 60 — Crabgrass, Large 20 25 65 35 20 60 4060 40 20 Crabgrass, Naked 20 35 70 20 — — 50 50 35 30 Dallisgrass 5 2060 10 35 15 25 10 10 0 Dayflower, VA 10 10 5 25 0 20 10 20 50 15 FieldBindweed 35 5 50 5 0 65 0 50 50 10 Foxtail, Green 5 10 70 0 20 20 5 2525 5 Goosegrass 40 35 65 20 50 40 30 40 35 40 Groundsel 100 85 100 70 —100 98 90 100 30 Guineagrass 10 20 50 10 5 10 10 25 20 20 Itchgrass 0 025 0 10 30 0 0 0 50 Johnsongrass 5 20 65 30 0 35 20 40 35 20 Kochia 0 50 5 — 0 25 25 20 10 Mallow 35 0 50 0 25 60 40 0 5 0 Morningglory 5 0 500 65 70 40 50 65 50 Nutsedge, Purple 0 0 0 0 0 5 0 0 0 0 Prickly Sida 6050 65 40 — — 70 50 50 30 Purslane 20 10 65 35 — 75 10 30 30 30Quackgrass 0 0 5 0 0 0 0 0 0 0 Ragweed 75 60 90 70 0 80 70 70 — 65Russian Thistle 20 0 — — — — — 0 0 0 Ryegrass, Italian 0 0 0 0 0 0 0 0 00 Sandbur 5 5 65 5 — 10 5 5 5 30 Signalgrass 0 5 50 5 0 20 20 5 0 0Sowthistle 90 95 80 70 35 100 90 90 100 90 Spanishneedles 35 35 75 30 6575 60 35 35 35 Surinam Grass 35 50 — 30 — — 30 60 — 30 Compound 250 gai/ha 243 Preemergence Barnyardgrass 100 Bermudagrass 100 Black Mustard100 Bluegrass 100 Crabgrass, Large 100 Crabgrass, Naked 100 Dallisgrass100 Dayflower, VA 100 Field Bindweed 100 Foxtail, Green 100 Goosegrass100 Guineagrass 100 Itchgrass 100 Johnsongrass 100 Kochia 100 Mallow 98Morningglory 100 Nutsedge, Purple 100 Prickly Sida 100 Purslane 100Quackgrass 98 Ragweed 100 Russian Thistle 100 Ryegrass, Italian 100Sandbur 100 Signalgrass 100 Spanishneedles 100 Surinam Grass 100Compounds 47 51 52 59 66 85 87 113 128 233 243 Preemergence 125 g ai/haBarnyardgrass 5 10 10 10 75 98 95 35 15 40 100 Bermudagrass 100 30 10090 5 100 98 85 75 85 100 Black Mustard 100 100 100 100 80 100 100 100 9565 100 Bluegrass 35 0 20 30 0 15 35 0 25 40 95 Chickweed — — 95 — 98 100— — — — — Crabgrass, Large 95 5 98 65 98 100 100 95 — 90 100 Crabgrass,Naked 98 0 80 95 25 98 100 100 75 65 100 Dallisgrass 75 90 95 75 95 9898 100 98 35 100 Dayflower, VA 50 0 40 35 5 95 65 65 25 100 100 FieldBindweed 35 0 50 60 20 98 70 90 98 85 100 Foxtail, Green 0 0 15 0 5 7010 20 0 0 100 Goosegrass 75 40 98 80 50 98 100 95 90 100 100 Guineagrass0 75 — 0 65 75 75 100 0 0 100 Itchgrass 0 0 5 20 0 50 20 0 20 20 50Johnsongrass 75 70 95 35 30 95 70 10 65 65 100 Kochia 100 50 35 0 90 95100 100 50 80 100 Mallow 98 65 — 65 75 98 100 90 100 60 80 Morningglory65 100 100 80 95 100 95 90 90 95 98 Nutsedge, Purple 35 5 40 80 70 95 7580 70 5 100 Prickly Sida 100 35 100 65 90 100 100 90 30 70 100 Purslane100 100 100 100 100 100 100 100 100 100 100 Quackgrass 0 0 20 0 0 20 0 00 0 85 Ragweed 100 95 98 100 0 100 98 98 100 98 100 Russian Thistle 10075 — 100 — — 100 100 100 100 100 Ryegrass, Italian 0 0 15 20 0 20 30 200 20 98 Sandbur 90 75 98 0 80 98 95 90 20 85 100 Signalgrass 90 10 90 55 95 75 90 5 35 95 Sowthistle 100 100 100 100 0 100 100 100 100 100 —Spanishneedles 95 98 98 90 95 100 98 95 100 95 100 Surinam Grass — — 98100 98 100 100 95 90 100 100 62 g ai/ha Barnyardgrass 5 0 0 0 5 95 50 05 5 100 Bermudagrass 50 0 90 40 5 100 98 70 65 85 100 Black Mustard 8075 80 60 35 98 100 80 85 20 100 Bluegrass 0 0 0 15 0 0 25 0 25 25 40Chickweed — — — — 90 100 — — — — — Crabgrass, Large 5 5 75 35 50 100 9595 60 25 100 Crabgrass, Naked 60 0 20 65 10 95 100 90 0 65 100Dallisgrass 65 10 50 65 5 95 80 50 65 0 100 Dayflower, VA 50 — 0 35 0 9065 50 10 100 100 Field Bindweed 0 0 20 20 0 70 40 65 35 85 100 Foxtail,Green 0 0 0 0 0 40 0 0 0 0 35 Goosegrass 5 40 80 20 30 75 95 75 65 98100 Guineagrass 0 0 50 0 0 70 50 100 0 0 100 Itchgrass 0 0 0 0 0 35 20 00 0 25 Johnsongrass 0 20 75 10 0 80 20 10 15 20 100 Kochia 100 0 25 0 6575 100 100 50 20 80 Mallow 65 0 — 65 5 95 80 5 70 0 50 Morningglory 2030 0 0 90 90 80 60 0 95 — Nutsedge, Purple 10 5 30 20 35 95 50 20 0 0 20Prickly Sida 65 20 50 5 5 100 100 70 25 0 100 Purslane 95 65 90 100 60100 100 100 100 100 95 Quackgrass 0 0 0 0 0 15 0 0 0 0 35 Ragweed 100 6570 90 0 100 98 80 90 95 100 Russian Thistle 50 75 — 90 — — 90 100 95 75100 Ryegrass, Italian 0 0 0 0 0 10 0 0 0 0 60 Sandbur 5 5 5 0 10 60 5065 20 50 100 Signalgrass 10 0 50 0 5 75 75 0 0 10 75 Sowthistle 100 9880 100 0 100 100 100 100 100 — Spanishneedles 95 90 95 0 85 98 85 — 9085 100 Surinam Grass 0 100 98 100 95 100 95 — 80 65 100 31 g ai/haBarnyardgrass 0 0 0 0 0 75 5 0 0 0 60 Bermudagrass 25 0 70 0 0 100 65 500 5 75 Black Mustard 65 50 20 40 5 60 75 0 60 0 80 Bluegrass 0 0 0 0 0 020 0 0 0 10 Chickweed — — — — 20 100 — — — — — Crabgrass, Large 0 5 2035 30 98 75 30 25 5 100 Crabgrass, Naked 0 0 0 0 0 95 80 0 0 0 100Dallisgrass 25 10 10 0 5 80 50 50 20 0 75 Dayflower, VA 35 0 0 0 0 10 050 0 80 90 Field Bindweed 0 0 — 0 0 70 0 20 0 0 100 Foxtail, Green 0 0 00 0 5 0 0 0 0 20 Goosegrass 0 20 60 5 0 75 35 25 5 95 100 Guineagrass 00 — 0 0 10 0 65 0 0 100 Itchgrass 0 0 0 0 0 15 20 0 0 0 10 Johnsongrass0 0 0 0 0 65 5 0 0 0 95 Kochia 50 — 25 0 65 20 98 70 0 0 — Mallow 0 0 —65 0 — — 5 70 0 0 Morningglory 0 0 0 0 0 70 — 60 0 80 90 Nutsedge,Purple 0 0 5 20 0 75 5 10 0 0 5 Prickly Sida 50 20 0 0 0 100 60 35 0 085 Purslane 0 50 60 100 0 100 100 100 0 0 75 Quackgrass 0 0 0 0 0 0 0 00 0 0 Ragweed 50 50 50 50 0 95 98 50 75 70 100 Russian Thistle — — — 90— — 75 65 0 65 100 Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 50 Sandbur 0 00 0 5 5 25 0 0 0 75 Signalgrass 0 0 0 0 5 60 0 0 0 0 — Sowthistle 65 7580 95 0 100 100 75 80 50 — Spanishneedles 95 0 70 0 60 98 65 0 0 50 100Surinam Grass — 98 98 90 80 100 50 40 35 5 100 Compounds 16 g ai/ha 4751 52 59 66 85 87 113 128 233 Preemergence Barnyardgrass 0 0 0 0 0 60 00 0 0 Bermudagrass 10 0 30 0 0 80 65 50 0 5 Black Mustard 0 0 0 20 0 5075 0 60 0 Bluegrass 0 0 0 0 0 0 20 0 0 0 Chickweed — — — — 0 90 — — — —Crabgrass, Large 0 0 0 0 15 95 50 20 0 0 Crabgrass, Naked 0 0 0 0 0 0 —0 0 0 Dallisgrass 0 0 5 0 0 50 50 5 0 0 Dayflower, VA 35 0 0 — 0 5 0 50— 0 Field Bindweed 0 0 20 0 0 50 0 0 0 0 Foxtail, Green 0 0 0 0 0 0 0 00 0 Goosegrass 0 20 5 0 0 65 35 25 0 70 Guineagrass 0 0 0 0 0 0 0 0 0 0Itchgrass 0 0 0 0 0 10 0 0 0 0 Johnsongrass 0 0 0 0 0 50 0 0 0 0 Kochia0 0 — 0 0 5 65 — 0 0 Mallow 0 0 — 0 0 80 — 0 — 0 Morningglory 0 0 0 0 0— 10 60 — 0 Nutsedge, Purple 0 0 0 0 0 70 0 0 0 0 Prickly Sida 0 0 0 0 090 50 0 0 0 Purslane 0 0 0 65 0 80 70 90 0 0 Quackgrass 0 0 0 0 0 0 0 00 0 Ragweed 0 35 30 0 0 90 30 0 0 50 Russian Thistle 0 — 0 — — — 50 0 —50 Ryegrass, Italian 0 0 0 0 0 0 0 0 0 0 Sandbur 0 0 0 0 0 5 0 0 0 0Signalgrass 0 0 0 0 0 5 0 0 0 0 Sowthistle 65 40 0 0 0 100 98 50 80 0Spanishneedles 0 0 35 0 0 90 0 0 0 0 Surinam Grass 0 90 0 5 0 98 0 — 0 0

Test E

Three plastic pots (ca. 16-cm diameter) for each application werepartially filled with sterilized Tama silt loam soil comprising a35:50:15 ratio of sand, silt and clay and 2.6% organic matter. Separateplantings for each of the three pots were as follows. Seeds from theU.S. of ducksalad (Heteranthera limosa), sedge (smallflower umbrellasedge, Cyperus difformis), ricefield bulrush (Scirpus mucronatus) andredstem (purple redstem, Ammannia coccinea), were planted into one 16-cmpot for each rate. Seeds from the U.S. of flatsedge (rice flatsedge,Cyperus iria), sprangletop (bearded (i.e. Brdd.) sprangletop, Leptochloafascicularis), one stand of 9 or 10 water seeded rice seedlings (Oryzasativa cv. ‘Japonica—M202’), and two stands of 3 or 4 transplanted riceseedlings (Oryza sativa cv. ‘Japonica—M202’) were planted into one 16-cmpot for each rate. Seeds from the U.S. of barnyardgrass (Echinochloacrus-galli), late watergrass (Echinochloa oryzicola), early watergrass(Echinochloa oryzoides) and junglerice (Echinochloa colona) were plantedinto one 16-cm pot for each rate. Plantings were sequential so that cropand weed species were at the 2.0 to 2.5-leaf stage at time of treatment.

Potted plants were grown in a greenhouse with day/night temperaturesettings of 30/27° C., and supplemental balanced lighting was providedto maintain a 16-hour photoperiod. Test pots were maintained in thegreenhouse until test completion.

At time of treatment, test pots were flooded to 3 cm above the soilsurface, treated by application of test compounds directly to the paddywater, and then maintained at that water depth for the duration of thetest. Effects of treatments on rice and weeds were visually evaluated bycomparison to untreated controls after 21 days. Plant response ratings,summarized in Table E, are based on a scale of 0 to 100 where 0 is noeffect and 100 is complete control. A dash (-) response means no testresult.

TABLE E Compounds 500 g ai/ha 4 19 Flood Barnyardgrass 60 85 Bulrush,Ricefield 80 75 Ducksalad 100 100 Flatsedge, Rice 90 100 Junglerice 5080 Redstem 85 85 Rice, Transplanted 15 65 Rice, Water Seeded 50 95Sedge, Umbrella 100 100 Sprangletop, Brdd. — 100 Watergrass, Early 65 85Watergrass, Late 60 55 Compounds 4 19 28 218 Flood 250 g ai/haBarnyardgrass 60 70 0 95 Bulrush, Ricefield 80 70 65 100 Ducksalad 100100 100 100 Flatsedge, Rice 40 95 45 75 Junglerice 25 65 0 100 Redstem80 90 90 80 Rice, Transplanted 0 40 15 10 Rice, Water Seeded 20 70 85 35Sedge, Umbrella 95 100 100 100 Sprangletop, Brdd. — 100 — 95 Watergrass,Early 60 65 20 60 Watergrass, Late 15 60 0 70 125 g ai/ha Barnyardgrass0 60 0 30 Bulrush, Ricefield 40 70 35 90 Ducksalad 90 95 80 95Flatsedge, Rice 0 40 0 70 Junglerice 0 50 0 65 Redstem 80 90 50 75 Rice,Transplanted 0 35 15 0 Rice, Water Seeded 10 40 65 20 Sedge, Umbrella 90100 90 100 Sprangletop, Brdd. — 95 — 70 Watergrass, Early 0 45 0 20Watergrass, Late 0 45 0 40 Compounds 64 g ai/ha 19 28 218 FloodBarnyardgrass 60 0 0 Bulrush, Ricefield 50 30 80 Ducksalad 85 0 85Flatsedge, Rice 40 0 70 Junglerice 0 0 0 Redstem 0 40 65 Rice,Transplanted 0 15 0 Rice, Water Seeded 0 60 0 Sedge, Umbrella 90 85 95Sprangletop, Brdd. 75 — 70 Watergrass, Early 20 0 20 Watergrass, Late 00 40 Compounds 32 g ai/ha 28 218 Flood Barnyardgrass 0 0 Bulrush,Ricefield 20 80 Ducksalad 0 80 Flatsedge, Rice 0 75 Junglerice 0 0Redstem 0 65 Rice, Transplanted 0 0 Rice, Water Seeded 45 15 Sedge,Umbrella 0 85 Sprangletop, Brdd. — 65 Watergrass, Early 0 0 Watergrass,Late 0 20

Test F

Test F evaluated the effect of combining compound 2 with bromoxynil. Thetest species for this experiment was Russian thistle (Salsola iberica),which was prepared by sowing seeds into a blend of loam soil and sand.Test chemicals were formulated in a non-phytotoxic solvent mixture thatincluded a surfactant and applied postemergence to plants ranging inheight from 12 to 20 cm.

Plants were grown in a greenhouse using supplemental lighting tomaintain a photoperiod of 16 hours; day and night temperatures rangedbetween 24-30° C. and 19-21° C., respectively. Treatments consisted ofCompound 2, bromoxynil, or their combination, using a spray volume of457 L/ha. Each treatment was replicated three times. Treated plants anduntreated controls were maintained in a greenhouse for 15 days, afterwhich time all plants were visually evaluated and compared to theuntreated controls. Plant responses were calculated as the mean of thethree replicates and summarized in Table F. Visual evaluations werebased on a scale of 0 to 100 where 0 is no effect and 100 is completecontrol. Colby's Equation was used to determine the herbicidal effectsexpected from the mixtures. Colby's Equation (Colby, S. R. “CalculatingSynergistic and Antagonistic Responses of Herbicide Combinations,”Weeds, 15(1), pp 20-22 (1967)) calculates the expected additive effectof herbicidal mixtures, and for two active ingredients is of the form:P _(a+b) =P _(a) +P _(b)−(P _(a) P _(b)/100)wherein P_(a+b) is the percentage effect of the mixture expected fromadditive contribution of the individual components:

-   -   P_(a) is the observed percentage effect of the first active        ingredient at the same use rate as in the mixture, and    -   P_(b) is the observed percentage effect of the second active        ingredient at the same use rate as in the mixture.        The results and additive effects expected from Colby's Equation        are listed in Table F1.

TABLE F1 Observed and Expected Results from Compound 2, Bromoxynil, ortheir combination. Postemergence Application Rate Russian (g a.i./ha)*Thistle Cmpd 2 Bromoxynil Obsd. Exp.  62 — 42 — 125 — 52 — —  70  8 — —140 13 —  62  70 93 47 125 140 95 58 *Application rates are grams ofactive ingredient per hectare (g a.i./ha). “Obsd.” is observed effect.“Exp.” is expected effect calculated from Colby's Equation.

The results in Table D1 suggest the combination of Compound 2 andbromoxynil have a synergistic action based on the observed injury beinggreater than the expected values as calculated by the Colby Equation foran additive effect.

What is claimed is:
 1. A compound of Formula 1Q including allstereoisomers, N-oxides, and salts thereof:

wherein A′ is a radical selected from the group consisting of

B¹ and B³ are each independently a radical selected from the groupconsisting of

B² is a radical selected from the group consisting of

R¹ is phenyl, phenylsulfonyl, —W¹(phenyl), —W¹(S-phenyl),—W¹(SO₂-phenyl), —W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionallysubstituted on ring members with up to five substituents selected fromR²¹; or -G or —W²G; or cyano, hydroxy, amino, —C(═O)OH, —C(═O)NHCN,—C(═O)NHOH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —NHCHO, C₁-C₁₀ alkyl, C₂-C₁₀alkenyl, C₂-C₁₀ alkynyl, C₁-C₁₀ haloalkyl, C₂-C₁₀ haloalkenyl, C₂-C₁₂haloalkynyl, C₃-C₁₂ cycloalkyl, C₃-C₁₂ halocycloalkyl, C₄-C₁₄alkylcycloalkyl, C₄-C₁₄ cycloalkylalkyl, C₆-C₁₈ cycloalkylcycloalkyl,C₄-C₁₄ halocycloalkylalkyl, C₅-C₁₆ alkylcycloalkylalkyl, C₃-C₁₂cycloalkenyl, C₃-C₁₂ halocycloalkenyl, C₂-C₁₂ alkoxyalkyl, C₃-C₁₂alkoxyalkenyl, C₄-C₁₄ alkylcycloalkyl, C₄-C₁₄ alkoxycycloalkyl, C₄-C₁₄cycloalkoxyalkyl, C₅-C₁₄ cycloalkoxyalkoxyalkyl, C₃-C₁₄alkoxyalkoxyalkyl, C₂-C₁₂ alkylthioalkyl, C₂-C₁₂ alkylsulfinylalkyl,C₂-C₁₂ alkylsulfonylalkyl, C₂-C₁₂ alkylaminoalkyl, C₃-C₁₄dialkylaminoalkyl, C₂-C₁₂ haloalkylaminoalkyl, C₄-C₁₄cycloalkylaminoalkyl, C₂-C₁₂ alkylcarbonyl, C₂-C₁₂ haloalkylcarbonyl,C₄-C₁₄ cycloalkylcarbonyl, C₂-C₁₂ alkoxycarbonyl, C₄-C₁₆cycloalkoxycarbonyl, C₅-C₁₄ cycloalkylalkoxycarbonyl, C₂-C₁₂alkylaminocarbonyl, C₃-C₁₄ dialkylaminocarbonyl, C₄-C₁₄cycloalkylaminocarbonyl, C₂-C₉ cyanoalkyl, C₁-C₁₀ hydroxyalkyl, C₄-C₁₄cycloalkenylalkyl, C₂-C₁₂ haloalkoxyalkyl, C₂-C₁₂ alkoxyhaloalkyl,C₂-C₁₂ haloalkoxyhaloalkyl, C₄-C₁₄ halocycloalkoxyalkyl, C₄-C₁₄cycloalkenyloxyalkyl, C₄-C₁₄ halocycloalkenyloxyalkyl, C₃-C₁₄dialkoxyalkyl, C₃-C₁₄ alkoxyalkylcarbonyl, C₃-C₁₄ alkoxycarbonylalkyl,C₂-C₁₂ haloalkoxycarbonyl, C₁-C₁₀ alkoxy, C₁-C₁₀ haloalkoxy, C₃-C₁₂cycloalkoxy, C₃-C₁₂ halocycloalkoxy, C₄-C₁₄ cycloalkylalkoxy, C₂-C₁₀alkenyloxy, C₂-C₁₀ haloalkenyloxy, C₂-C₁₀ alkynyloxy, C₃-C₁₀haloalkynyloxy, C₂-C₁₂ alkoxyalkoxy, C₂-C₁₂ alkylcarbonyloxy, C₂-C₁₂haloalkylcarbonyloxy, C₄-C₁₄ cycloalkylcarbonyloxy, C₃-C₁₄alkylcarbonylalkoxy, C₁-C₁₀ alkylthio, C₁-C₁₀ haloalkylthio, C₃-C₁₂cycloalkylthio, C₁-C₁₀ alkylsulfinyl, C₁-C₁₀ haloalkylsulfinyl, C₁-C₁₀alkylsulfonyl, C₁-C₁₀ haloalkylsulfonyl, C₃-C₁₂ cycloalkylsulfonyl,C₂-C₁₂ alkylcarbonylthio, C₂-C₁₂ alkyl(thiocarbonyl)thio, C₃-C₁₂cycloalkylsulfinyl, C₁-C₁₀ alkylaminosulfonyl, C₂-C₁₂dialkylaminosulfonyl, C₁-C₁₀ alkylamino, C₂-C₁₂ dialkylamino, C₁-C₁₀haloalkylamino, C₂-C₁₂ halodialkylamino, C₃-C₁₂ cycloalkylamino, C₂-C₁₂alkylcarbonylamino, C₂-C₁₂ haloalkylcarbonylamino, C₁-C₁₀alkylsulfonylamino, C₁-C₁₀ haloalkylsulfonylamino or C₄-C₁₄cycloalkyl(alkyl)amino; W¹ is C₁-C₆ alkylene, C₂-C₆ alkenylene or C₂-C₆alkynylene; W² is C₁-C₆ alkylene; R² is phenyl or —W³(phenyl), eachoptionally substituted on ring members with up to five substituentsselected from R²¹; or -G or —W⁴G; or H, cyano, hydroxy, amino, nitro,—CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN, —C(═O)NHOH, —SH,—SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —SF₅, —NHCHO, —NHNH₂, —NHOH, —NHCN,—NHC(═O)NH₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl,C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₂-C₈alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈alkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂cycloalkylalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₂-C₅ cyanoalkyl,C₁-C₆ hydroxyalkyl, C₄-C₁₀ cycloalkenylalkyl, C₂-C₈ haloalkoxyalkyl,C₂-C₈ alkoxyhaloalkyl, C₂-C₈ haloalkoxyhaloalkyl, C₄-C₁₀halocycloalkoxyalkyl, C₄-C₁₀ cycloalkenyloxyalkyl, C₄-C₁₀halocycloalkenyloxyalkyl, C₃-C₁₀ dialkoxyalkyl, C₃-C₁₀alkoxyalkylcarbonyl, C₃-C₁₀ alkoxycarbonylalkyl, C₂-C₈haloalkoxycarbonyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy,C₃-C₈ halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆haloalkenyloxy, C₂-C₆ alkynyloxy, C₃-C₆ haloalkynyloxy, C₂-C₈alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀cycloalkylcarbonyloxy, C₃-C₁₀ alkylcarbonylalkoxy, C₁-C₆ alkylthio,C₁-C₆ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈cycloalkylsulfonyl, C₃-C₈ trialkylsilyl, C₃-C₈ cycloalkenyloxy, C₃-C₈halocycloalkenyloxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈ alkoxyhaloalkoxy,C₂-C₈ haloalkoxyhaloalkoxy, C₃-C₁₀ alkoxycarbonylalkoxy, C₂-C₈alkyl(thiocarbonyl)oxy, C₂-C₈ alkylcarbonylthio, C₂-C₈alkyl(thiocarbonyl)thio, C₃-C₈ cycloalkylsulfinyl, C₁-C₆alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀halotrialkylsilyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₁-C₆haloalkylamino, C₂-C₈ halodialkylamino, C₃-C₈ cycloalkylamino, C₂-C₈alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₁-C₆alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino or C₄-C₁₀cycloalkyl(alkyl)amino; or R¹ and R² are taken together along with theatoms to which they are attached to make a 5-, 6- or 7-memberedunsaturated, partially unsaturated or fully unsaturated ring along withmembers consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfuratoms or up to two —S(O)—, —S(O)₂—, —C(O)— groups optionally substitutedwith halogen, cyano, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl on carbon atom ringmembers and H or C₁-C₆ alkyl on nitrogen ring members; W³ is C₁-C₆alkylene, C₂-C₆ alkenylene or C₂-C₆ alkynylene; W⁴ is C₁-C₆ alkylene; R⁹is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₆-C₁₄cycloalkylcycloalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈alkylthioalkyl; R¹⁰ is H, halogen, cyano, hydroxy, amino, nitro, SH,—SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, —NHCHO, —NHNH₂, —N₃,—NHOH, —NHCN, —NHC(═O)NH₂, —N═C═O, —N═C═S, C₁-C₆ alkyl, C₂-C₆ alkenyl,C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl,C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl, C₄-C₁₀halocycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl,C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl,C₃-C₁₀ alkoxyalkoxyalkyl or C₂-C₈ alkylthioalkyl; n is 0, 1, or 2; eachR¹⁴, R¹⁵, R¹⁸ and R¹⁹ is independently H, halogen, cyano, hydroxy orC₁-C₆ alkyl; or a pair of R¹⁴ and R¹⁸ is taken together as C₂-C₆alkylene or C₂-C₆ alkenylene; R²⁰ is H, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₁-C₆alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₈ cycloalkyl; T is C₁-C₆alkylene or C₂-C₆ alkenylene; each G is independently a 5- or 6-memberedheterocyclic ring or an 8-, 9- or 10-membered fused bicyclic ringsystem, each ring or ring system optionally substituted with up to fivesubstituents selected from R²¹ on carbon ring members and R²² onnitrogen ring members; each R²¹ is independently halogen, cyano,hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —C(═S)NH₂, —C(═O)NHCN,—C(═O)NHOH, —SH, —SO₂NH₂, —SO₂NHCN, —SO₂NHOH, —OCN, —SCN, —SF₅, C₁-C₆alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₂-C₆ haloalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl, C₂-C₈alkoxyhaloalkyl, C₂-C₅ cyanoalkyl, C₁-C₆ hydroxyalkyl, C₁-C₆ alkoxy,C₁-C₆ haloalkoxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀cycloalkylalkoxy, C₂-C₆ alkenyloxy, C₂-C₆ haloalkenyloxy, C₂-C₈alkoxyalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₃-C₈cycloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₁-C₆haloalkylamino, C₂-C₈ halodialkylamino or C₃-C₈ cycloalkylamino; andeach R²² is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl,C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl or C₂-C₈ alkoxyalkyl.
 2. A compound ofclaim 1 wherein A′ is A′-1, A′-3 or A′-5; B¹ is C-1; B² is C-3; B³ isC-1; R¹ is phenyl, —W¹(phenyl), —W¹(S-phenyl), —W¹(SO₂-phenyl),—W²(SO₂CH₂-phenyl) or —W²(SCH₂-phenyl), each optionally substituted onring members with up to five substituents selected from R²¹; or —G or—W²G; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl,C₂-C₆ haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈alkoxyalkyl, C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl, C₄-C₁₀alkoxycycloalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₁₂alkylsulfinylalkyl or C₂-C₈ alkylsulfonylalkyl; W¹ is C₁-C₆ alkylene; W²is —CH₂—; R² is phenyl or —W³(phenyl), each optionally substituted onring members with up to two substituents selected from R²¹; or —G or; orC₁-C₆ alkyl or C₃-C₈ cycloalkyl; W³ is —CH₂—; R¹⁴ and R¹⁸ are H or C₁-C₆alkyl; each R¹⁵ and R¹⁹ is H or CH₃; T is —CH₂CH₂— or —CH═CH—; G is

r is 0, 1, 2 or 3; and each R²¹ is independently halogen, nitro, C₁-C₆alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy or C₁-C₆alkylthio.
 3. A compound of claim 2 wherein A′ is A′-1 or A′-3; R¹ isphenyl or —W¹(phenyl), each optionally substituted on ring members withup to two substituents selected from R²¹; or —G or —W²G; or C₁-C₆ alkyl,C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₃-C₈cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂ alkylcycloalkylalkyl, C₃-C₈cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl C₃-C₁₀alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl or C₄-C₁₀ alkoxycycloalkyl; W¹ is—CH₂—; R² is phenyl optionally substituted on ring members with up totwo substituents selected from R²¹; or —G; or C₁-C₆ alkyl or C₃-C₈cycloalkyl; R¹⁴ and R¹⁸ are H or CH₃; each R¹⁵ and R¹⁹ is H; G is G-19or G-20; each R²¹ is independently fluorine, chlorine, bromine, CH₃,CF₃, OCH₃, OCF₃ or SCH₃.
 4. A compound of claim 2 wherein A′ is A′-1 orA′-3; R¹ is phenyl or —W¹(phenyl), each optionally substituted on ringmembers with up to two substituents selected from R²¹; or —G or —W²G; orC₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₃-C₈ cycloalkyl, C₄-C₁₀ cycloalkylalkyl, C₅-C₁₂alkylcycloalkylalkyl, C₃-C₈ cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈alkoxyalkyl C₃-C₁₀ alkoxyalkenyl, C₄-C₁₀ alkylcycloalkyl or C₄-C₁₀alkoxycycloalkyl; W¹ is —CH₂—; R² is phenyl optionally substituted onring members with up to two substituents selected from R²¹; or —G; orC₁-C₆ alkyl or C₃-C₈ cycloalkyl; R¹⁴ and R¹⁸ are H or CH₃; each R¹⁵ andR¹⁹ is H; G is G-2, G-3 or G-15; and each R²¹ is independently fluorine,chlorine, bromine, CH₃, CF₃, OCH₃, OCF₃ or SCH₃.
 5. A compound of claim2 wherein A′ is A′-3; R¹ is phenyl, 2-fluorophenyl, 3-fluorophenyl,4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl,4-methylphenyl, 4-ethylphenyl, 2-methylphenyl, 3-methoxyphenyl,4-methoxyphenyl, 3,5-dimethylphenyl, 3,4-dimethoxyphenyl,2,3-dimethylphenyl, 3-fluoro-2-methylphenyl, 4-fluoro-3-methylphenyl or5-chloro-2-methylphenyl; R² is phenyl, 2-methylphenyl, 3-methylphenyl,3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or3,5-difluorophenyl; T is —CH₂CH₂—; R¹⁸ is H; and R¹⁹ is H.
 6. A compoundof claim 2 wherein A′ is A′-3; R¹ is n-Pr, i-Pr, n-Bu, c-hexyl,—CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or —CH₂CH₂OCH₂CH₃; R² is phenyl,2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl,4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl; and T is —CH₂CH₂—;R¹⁸ is H; and R¹⁹ is H.
 7. A compound of claim 2 wherein A is A′-3; R¹is —CH₂CH₂CH₂OCH₃; R² is 3-methoxyphenyl; T is —CH₂CH₂—; R¹⁸ is H; andR¹⁹ is H.
 8. A compound of claim 2 wherein A′ is A′-1; R¹ is phenyl,2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl,3-chlorophenyl, 4-chlorophenyl, 4-methylphenyl, 4-ethylphenyl,2-methylphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,5-dimethylphenyl,3,4-dimethoxyphenyl, 2,3-dimethylphenyl, 3-fluoro-2-methylphenyl,4-fluoro-3-methylphenyl or 5-chloro-2-methylphenyl; R² is phenyl,2-methylphenyl, 3-methylphenyl, 3-bromophenyl, 3-chlorophenyl,4-chlorophenyl, 3-fluorophenyl or 3,5-difluorophenyl; R¹⁴ and R¹⁸ are H;and R¹⁵ and R¹⁹ are H.
 9. A compound of claim 2 wherein A′ is A′-1; R¹is n-Pr, i-Pr, n-Bu, c-hexyl, —CH₂CH₂OCH₃, —CH₂CH₂CH₂OCH₃ or—CH₂CH₂OCH₂CH₃; R² is phenyl, 2-methylphenyl, 3-methylphenyl,3-bromophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl or3,5-difluorophenyl; R¹⁴ and R¹⁸ are H; and R¹⁵ and R¹⁹ are H.
 10. Acompound of claim 2 wherein A is A′-1; R¹ is —CH₂CH₂CH₂OCH₃; R² is3-methoxyphenyl; R¹⁴ and R¹⁸ are H; and R¹⁵ and R¹⁹ are H.